3-(pyrrolidin-3-yl)-1H-indole → HCID 10394324, compound

HRID 2357487Notes

Reaction equation

HRID 2357487 reaction equation
C1(O[C:8](=[O:26])[NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([N:23]([CH3:25])[CH3:24])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)C=CC=CC=1.[NH:27]1[CH2:31][CH2:30][CH:29]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[NH:34][CH:33]=2)[CH2:28]1>O1CCOCC1>[CH3:25][N:23]([CH3:24])[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12][CH:11]([CH2:10][NH:9][C:8]([N:27]2[CH2:31][CH2:30][CH:29]([C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][CH:33]=3)[CH2:28]2)=[O:26])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 184096763-(pyrrolidin-3-yl)-1H-indoleHCID 67531743(4-Dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid phenyl ester

Product 1

HCID 10394324HCID 10394324, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The diastereoisomer mixture of (4-dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid phenyl ester (519 mg, 1.47 mmole) was added to a solution of 3-pyrrolidine-3-yl-1H-indole (274 mg, 1.47 mmole) in dioxane (12 ml). The reaction mixture was then boiled under reflux for 12 hours. The reaction mixture was worked up by distilling off the solvent. The residue contained, apart from phenol, also the two diastereoisomers of 3-(1H-indol-3-yl)pyrrolidine-1-carboxylic acid-(4-dimethyl amino-4-phenylcyclohexylmethyl)-amide. The diastereoisomers were separated and purified by flash chromatography on silica gel (50 g). Methanol/EE (1:1; 1000 ml) was used as eluent. The non-polar diastereoisomer of 3-(1H-indol-3-yl)pyrrolidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (234 mg, m.p. 101°-103° C., 36%) and the polar diastereoisomer of 3-(1H-indol-3-yl)pyrrolidine-1-carboxylic acid-(4-dimethylamino-4-phenylcyclohexylmethyl)-amide (244 mg, m.p. 103°-106° C., 37%) were thereby obtained in pure form.

Workup

  1. temperatureunder reflux for 12 hours
  2. distillationby distilling off the solvent
  3. customThe diastereoisomers were separated
  4. custompurified by flash chromatography on silica gel (50 g)

Sources & evidence

ORD record
ord-443b36f3b8fb41cfade0df64bd8631e0
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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