GB809488A - Carbazole derivatives and process for the production thereof - Google Patents

Carbazole derivatives and process for the production thereof

Info

Publication number
GB809488A
GB809488A GB303057A GB303057A GB809488A GB 809488 A GB809488 A GB 809488A GB 303057 A GB303057 A GB 303057A GB 303057 A GB303057 A GB 303057A GB 809488 A GB809488 A GB 809488A
Authority
GB
United Kingdom
Prior art keywords
carbazole
methyl
general formula
piperidylmethyl
ethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB303057A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chemische Fabrik Promonta GmbH
Original Assignee
Chemische Fabrik Promonta GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chemische Fabrik Promonta GmbH filed Critical Chemische Fabrik Promonta GmbH
Publication of GB809488A publication Critical patent/GB809488A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises carbazole derivatives of the general formula <FORM:0809488/IV (b)/1> (wherein X1 and X2, which may be the same or different, are hydrogen or halogen atoms, or lower alkyl or lower alkoxy groups having from 1 to 4 carbon atoms, x is 0, 1 or 2, the piperidine radical being substituted in the 3- or 4-position when x is 0 and in the 2-, 3- or 4-position when x is 1 or 2, and R is an alkyl group), their acid addition salts, and their preparation by condensing a carbazole of the general formula (II) <FORM:0809488/IV (b)/2> with an N-alkylated-piperidyl derivative of the general formula <FORM:0809488/IV (b)/3> (substituted as above). The reaction is carried out in the presence of an alkali metal condensing agent, e.g. an alkali metal or hydride, amide or oxide thereof, in an inert organic solvent, e.g. an aromatic hydrocarbon, or high-boiling ether (preferably having a boiling-point between 120 DEG and 150 DEG C.); alternatively, an N-alkylatedpiperidyl derivative of the general formula above is condensed with a Grignard derivative of a carbazole of the general formula (II). The products may be converted into acid addition salts if desired. Examples describe the preparation of 9 - (N - methylpiperidyl - 3 - and - 4)-carbazole, 9 - (N - R - 3 - piperidylmethyl)-carbazole (R=methyl, ethyl, n-propyl), 9-(N-R-4-piperidylmethyl)-carbazole (R=methyl, ethyl), 9 - (N - methyl - 2 - piperidylmethyl) - carbazole, 9 - [b - (N - methylpiperidyl - 2) - ethyl] - carbazole, 9 - (N - methyl - 21 - piperidylmethyl) - 3 - methyl-, -3-methoxy- and -2-chloro-carbazole.
GB303057A 1956-02-01 1957-01-28 Carbazole derivatives and process for the production thereof Expired GB809488A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC12512A DE1083824B (en) 1956-02-01 1956-02-01 Process for the preparation of N-substituted carbazoles and their salts

Publications (1)

Publication Number Publication Date
GB809488A true GB809488A (en) 1959-02-25

Family

ID=7015227

Family Applications (1)

Application Number Title Priority Date Filing Date
GB303057A Expired GB809488A (en) 1956-02-01 1957-01-28 Carbazole derivatives and process for the production thereof

Country Status (3)

Country Link
CH (1) CH354780A (en)
DE (1) DE1083824B (en)
GB (1) GB809488A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005036A1 (en) * 1991-09-06 1993-03-18 Taisho Pharmaceutical Co., Ltd. N-substituted carbazole derivative
US20150368226A1 (en) * 2013-01-10 2015-12-24 Merck Patent Gmbh Piperidinylcarbazoles

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005036A1 (en) * 1991-09-06 1993-03-18 Taisho Pharmaceutical Co., Ltd. N-substituted carbazole derivative
US20150368226A1 (en) * 2013-01-10 2015-12-24 Merck Patent Gmbh Piperidinylcarbazoles
US9908863B2 (en) * 2013-01-10 2018-03-06 Merck Patent Gmbh Piperidinylcarbazoles

Also Published As

Publication number Publication date
DE1083824B (en) 1960-06-23
CH354780A (en) 1961-06-15

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