Cyclopentylamine → HCID 44159567, compound

HRID 517843Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]([O:15]CC)=O)[C:6]3[CH2:18][CH2:19][N:20]([CH3:22])[CH2:21][C:5]=3[C:4]=2[CH:3]=1.[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]([NH:28][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:15])[C:6]3[CH2:18][CH2:19][N:20]([CH3:22])[CH2:21][C:5]=3[C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 44159333Ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate

Product 1

HCID 44159567HCID 44159567, compound

Conditions

Temperature: 120 °C

Procedure

A mixture of ethyl 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)propanoate (CD17) (100 mg) and cyclopentylamine (1 ml) was heated at 120° C. for 15 h to obtain 3-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-N-cyclopentylpropanamide (CD32) after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF.

Sources & evidence

ORD record: ord-af8fe45b3d1541898f9ef6da552f455e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115137B2

Reaction notes

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