Piperidine → Methyl 2-nitro-5-(piperidin-1-ylmethyl)benzoate

HRID 425964Notes

Reaction equation

HRID 425964 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N+:13]([O-:15])=[O:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C>[N+:13]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 13399988Methyl 5-(bromomethyl)-2-nitrobenzoate

Product 1

HCID 66703610Methyl 2-nitro-5-(piperidin-1-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 5-(bromomethyl)-2-nitrobenzoate was added to a DMF suspension of potassium carbonate and piperidine, followed by stirring at room temperature to obtain methyl 2-nitro-5-(piperidin-1-ylmethyl)benzoate (Dat, ES: 279). This compound was dissolved in acetic acid, iron powder was added thereto, followed by stirring at 60° C. to obtain methyl 2-amino-5-(piperidin-1-ylmethyl)benzoate (Dat, F: 249). Cyclohexanone and sodium triacetoxyborohydride were added to an acetic acid solution of this compound, followed by stirring at room temperature. By post-treating the reaction liquid, methyl 2-(cyclohexylamino)-5-(piperidin-1-ylmethyl)benzoate was obtained.

Sources & evidence

ORD record
ord-f198f7ad2b824c818969ebb9cdadcf9c
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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