Benzylamine → N-benzyl-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide

HRID 517839Notes

Reaction equation

HRID 517839 reaction equation
[CH3:1][N:2]1[CH2:19][CH2:18][C:5]2[N:6]([CH2:14][C:15]([OH:17])=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.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:31]([NH:38][C:15](=[O:17])[CH2:14][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:19][CH2:18][C:5]1=2)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 591616282-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetic acid

Product 1

HCID 44159455N-benzyl-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide

Procedure

2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetic acid (CD58) was mixed with EDCI and benzylamine and the reaction mixture was stirred for 16 h to obtain N-benzyl-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide 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-e62576246a14467492cbb8a6b7f09c99
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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