Indole-3-Carboxylic Acid → N-[(1-Methyl-4-piperidyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

HRID 609611Notes

Reaction equation

HRID 609611 reaction equation
N1C2C(=CC=CC=2)[C:3]([C:10](O)=[O:11])=[CH:2]1.CN1CCC(CN)CC1.[CH2:22]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][NH:33][C:34]([C:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][CH:37]=2)=[O:35])[CH2:28][CH2:27]1)CCC>>[CH3:22][N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][NH:33][C:34]([C:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][CH:37]=2)=[O:35])[CH2:28][CH2:27]1.[CH3:22][N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][NH:33][C:34]([C:36]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:38]3[CH2:2][CH2:3][CH2:10][O:11][C:37]=23)=[O:35])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 69867Indole-3-Carboxylic AcidHCID 815741-Methylpiperidine-4-methylamineHCID 10591304N-[(1-n butyl-4-piperidyl)methyl] indole-3-carboxamide

Product 2

HCID 19599445N-[(1-Methyl-4-piperidyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamideHCID 19599451N-[(1-Methyl-4-piperidyl)methyl] indole-3-carboxamide

Procedure

N-[(1-Methyl-4-piperidyl)methyl]indole-3-carboxamide was prepared from indole-3-carboxylic acid and N-(1-methyl-4-piperidyl)methylamine using an analogous method to Description 1b and then converted to the title compound using an similar procedure to Example 3 (method 2).

Sources & evidence

ORD record
ord-40dee26818a24ab9b1c5fb4a1554a93e
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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