Triethylamine → 1-BOC-4-DIMETHYLCARBAMOYLPIPERIDINE

HRID 390845Notes

Reaction equation

HRID 390845 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17](N1C=CN=C1)([N:19]1C=CN=[CH:20]1)=O.Cl.CNC.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](=[O:13])[N:19]([CH3:20])[CH3:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 110215051-BOC-4-DIMETHYLCARBAMOYLPIPERIDINE

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of BOC-isonipecotic acid (400 mg) in N,N-dimethylformamide (4 mL) was added 1,1′-carbonyldiimidazole (560 mg). The reaction mixture was stirred overnight and then dimethylamine hydrochloride (280 mg) and triethylamine (0.48 mL) were added. After 5 hours the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield 4-dimethylcarbamoyl-piperidine-1-carboxylic acid tert-butyl ester. Removal of the BOC group with HCl yielded piperidine-4-carboxylic acid dimethylamide, which was isolated as the hydrochloride salt.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3084832a30dc406d95698d680c9f642d
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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