Triethylamine → Hydrochloric Acid

HRID 390822

Reaction equation

HRID 390822 reaction equation
C([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[C:17](N1C=CN=C1)([N:19]1C=CN=C1)=O.[ClH:29].CN.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[ClH:29].[CH3:17][NH:19][C:12]([CH:11]1[CH2:15][CH2:16][NH:8][CH2:9][CH2:10]1)=[O:13]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 6364545Methylamine hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 2760460N-methylpiperidine-4-carboxamide

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 methylamine 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. Treatment with HCl yielded piperidine-4-carboxylic acid methylamide, 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-a70916512f6146d395d309e2ba3bcdd5
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Linked notes

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