Benzylamine → N-Benzyl-3-(5-fluoro-1-methyl-1H-indol-3-yl)-cyclopentylamine

HRID 1824008Notes

Reaction equation

HRID 1824008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[CH:12]1[CH2:16][CH2:15][C:14](=O)[CH2:13]1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:25][CH:14]1[CH2:15][CH2:16][CH:12]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[N:7]([CH3:11])[CH:6]=2)[CH2:13]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 221491463-(5-fluoro-1-methyl-1H-indol-3-yl)cyclopentanone

Product 1

HCID 22149139N-Benzyl-3-(5-fluoro-1-methyl-1H-indol-3-yl)-cyclopentylamineYield 101.6%

Procedure

This compound was prepared in the same manner as for Intermediate 6, using 3-(5-fluoro-1-methyl-1H-indol-3-yl)-cyclopentanone (1.25 g, 5.19 mmol) and benzylamine (0.66 g, 6.2 mmol) to afford 1.7 g of the desired product as a mixture of cis and trans isomers. Flash chromatography on silica gel (3% 2 M NH3 in methanol/ethyl acetate) afforded 0.4 g (23%) of the cis isomer (first eluting) and 0.45 g (27%) of the trans isomer.

Sources & evidence

ORD record
ord-485be8d3b6dd4a07bcb396cc2373444b
Source dataset
uspto-grants-2006_05
Patent number
US07041697B2

Reaction notes

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