Triethylamine → 1-BOC-4-DIMETHYLCARBAMOYLPIPERIDINE

HRID 2353122Notes

Reaction equation

HRID 2353122 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=O)C.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

Amine preparation: to a stirring solution of BOC-isonipecotic acid (400 mg) in DMF (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 h the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent was removed in vacuo to yield 4-dimethylcarbamoyl-piperidine-1-carboxylic acid tert-butyl ester. Removal of the BOC group with HCl yielded the desired compound, which was isolated as the hydrochloride salt.

Workup

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

Sources & evidence

ORD record
ord-733c899f52a148329df7d69462c7fa5d
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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