1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44159566, compound

HRID 517850Notes

Reaction equation

HRID 517850 reaction equation
[CH3:1][N:2]1[CH2:20][CH2:19][C:5]2[N:6]([CH2:14][CH2:15][C:16]([OH:18])=O)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.CCN=C=NCCCN(C)C.[CH:32]1([CH2:38][NH2:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>ClCCl>[CH:32]1([CH2:38][NH:39][C:16](=[O:18])[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])[CH2:20][CH2:19][C:5]2=3)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76688CyclohexanemethylamineHCID 59161623HCID 59161623, compound

Product 1

HCID 44159566HCID 44159566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanoic acid was mixed with EDCI and cyclohexylmethanamine in dichloromethane and the reaction mixture was stirred for 16 h to obtain N-(cyclohexylmethyl)-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. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF.

Sources & evidence

ORD record
ord-e6a535d8d3f3492e9b2f8a8a11b5a630
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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