Methanol → N,N-dimethylpiperidine-4-carboxamide

HRID 1622323Notes

Reaction equation

HRID 1622323 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:18])[N:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.CO.C(Cl)(Cl)[Cl:22]>O1CCOCC1>[ClH:22].[CH3:16][N:15]([CH3:17])[C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:18]

Participants

6

Reactant 3

HCID 887MethanolHCID 6212ChloroformHCID 110215051-BOC-4-DIMETHYLCARBAMOYLPIPERIDINE

Product 2

HCID 313Hydrochloric AcidHCID 411689N,N-dimethylpiperidine-4-carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

General procedure B was followed using tert-butyl-4-(dimethylcarbamoyl)piperidine-1-carboxylate 2 (0.16 g, 0.60 mmol), MeOH (2.5 mL) and a 4 M solution of hydrogen chloride in 1,4-dioxane (2.5 mL) to furnish the title compound as a pale yellow oil (67 mg, 71%), umax (CHCl3)/cm−1 3003, 2947, 1625, 1497, 1401, 1320, 1240, 1137, 1105; m/z (ESI) C8H17N2O requires 157.1335, found [M+H]+ 157.1338.

Sources & evidence

ORD record
ord-b8cf5de77d834bf384555bc416e8df4e
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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