Iodocyclopentane → 3-Cyclopentyl-1H-indol-6-ylamine

HRID 469973Notes

Reaction equation

HRID 469973 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.I[CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CC#N>[CH:14]1([C:8]2[C:7]3[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=3)[NH:10][CH:9]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 73784IodocyclopentaneHCID 785026-Nitro-1H-indole

Product 1

HCID 574702013-Cyclopentyl-1H-indol-6-ylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Cyclopentyl-1H-indol-6-ylamine (B-15) was synthesized following the general scheme above starting from 6-nitroindole and iodo-cyclopentane. Overall yield (16%). HPLC ret. time 2.39 min, 10-99% CH3CN, 5 min run; ESI-MS 201.5 m/z (MH+).

Workup

  1. customOverall yield (16%)

Sources & evidence

ORD record
ord-e62f0fc9190445b38110e06d6a803d69
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

Loading…