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Dicyclohexylcarbodiimide → 8-[4-(6-Chloro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-ylcarbonyl]-3,6,7,8-tetrahydrocyclopent[e]indole

HRID 275711
Notes
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Reaction equation

HRID 275711 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]([C:13]([OH:15])=O)[CH2:11][CH2:12][C:7]=3[CH:6]=[CH:5][C:4]=2[NH:3][CH:2]=1.[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C1COCC1>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]3[CH2:27][CH2:28][N:29]([C:13]([CH:10]4[C:8]5[C:9]6[CH:1]=[CH:2][NH:3][C:4]=6[CH:5]=[CH:6][C:7]=5[CH2:12][CH2:11]4)=[O:15])[CH2:30][CH:31]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 185458923,6,7,8-Tetrahydrocyclopent[e]indole-8-carboxylic acid

Product 1

HCID 185457998-[4-(6-Chloro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-ylcarbonyl]-3,6,7,8-tetrahydrocyclopent[e]indoleYield 38.5%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14a (1.4 g), 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1-H-indole (1.6 g), dicyclohexylcarbodiimid (1.9 g), and 4-dimethylaminopyridine (0.1 g) in THF (100 ml) was stirred for 24 hours at room temperature. The mixture was filtered and evaporated in vacuo. The residue was purified on silica gel eluted with ethyl acetate-heptane (3:2) giving 1.1 g of the title product as an amorpheous powder.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was purified on silica gel
  4. washeluted with ethyl acetate-heptane (3:2)

Sources & evidence

ORD record
ord-d105dae424614a72a1a025e90ba688de
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06352988B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes