4-(Dimethylamino)Benzaldehyde → Ethyl 1,2,3,4-Tetrahydro-l-(4-Dimethylaminophenyl)-9H-Pyrido (3,4-b)Indole-3-Carboxylate

HRID 324385

Reaction equation

HRID 324385 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6])[CH3:2].[CH3:18][N:19]([CH3:28])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1>>[CH3:18][N:19]([CH3:28])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]2[C:9]3[NH:10][C:11]4[C:16]([C:8]=3[CH2:7][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:17])[NH:6]2)=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 81996L-Tryptophan, ethyl ester

Product 1

HCID 22677859Ethyl 1,2,3,4-Tetrahydro-l-(4-Dimethylaminophenyl)-9H-Pyrido (3,4-b)Indole-3-Carboxylate

Procedure

The same method as employed in the preparation of Intermediates 1 and 2 but starting from racemic tryptophan ethyl ester and 4-dimethylaminobenzaldehyde gave the title compound as white crystals m.p.: 170° C.

Sources & evidence

ORD record
ord-6730f08bcdcc4db7bc759a20835b6fa7
Source dataset
uspto-grants-2001_04
Patent number
US06218400B1

Linked notes

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