Benzylamine → N-Benzyl-3-(1H-indole-3-yl)-cyclopentylamine

HRID 1072448Notes

Reaction equation

HRID 1072448 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:14][CH2:13][C:12](=O)[CH2:11]2)=[CH:2]1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([NH:23][CH:12]1[CH2:13][CH2:14][CH:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 113446533-(1H-Indol-3-yl)cyclopentanone

Product 1

HCID 22386577N-Benzyl-3-(1H-indole-3-yl)-cyclopentylamineYield 107.9%

Procedure

This compound was prepared in similar manner as for Intermediate 17, using 3-(1H-indol-3-yl)-cyclopentanone (3.0 g, 15 mmol) and benzylamine (1.95 g, 18 mmol) to give 4.7 g of the desired product as a mixture of cis and trans isomers, which were separated by flash chromatography to afford 0.6 g of the cis isomer (first eluting) and 1.0 g of the trans isomer.

Sources & evidence

ORD record
ord-14ade635b162461e8faddbdc2f9c8cdb
Source dataset
uspto-grants-2005_06
Patent number
US06911445B2

Reaction notes

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