Cyclopentylamine → HCID 44159095, compound

HRID 517827Notes

Reaction equation

[CH3:1][N:2]1[CH2:22][CH2:21][C:5]2[N:6]([CH2:14][CH2:15][C:16](OCC)=[O:17])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH:23]1([NH:28][C:16](=[O:17])[CH2:15][CH2:14][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:22][CH2:21][C:5]2=3)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 23932524HCID 23932524, compound

Product 1

HCID 44159095HCID 44159095, compoundYield 15.2%

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanoate (100 mg, 0.33 mmol) and cyclopentylamine (1 ml, 10 mmol) was heated at 100-120° C. for 3-4 h to obtain 17 mg of N-cyclopentyl-3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanamide after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient.

Sources & evidence

ORD record: ord-72a079384ced47c996dd591d48b67813
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115137B2

Reaction notes

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