Formamide → 1-Benzylpiperidine-4-carboxamide

HRID 54555

Reaction equation

HRID 54555 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH2:21])=O.C[O-].[Na+]>CN(C)C=O.CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:16])[NH2:21])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 713FormamideHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 7831561-Benzylpiperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-benzyl-4-ethoxycarbonylpiperidine (6.88 g) and formamide (3.71 ml) in N,N-dimethylformamide (30 ml) was added 28% sodium methoxide solution in methanol (4.0 ml) at 100° C. under stirring. After stirring at 100° C. for 1 hour, the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine and dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ether to give 1-benzyl-4-carbamoylpiperidine (2.8 g).

Workup

  1. stirringAfter stirring at 100° C. for 1 hour
  2. customthe mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-f586b6b243224d18bbe6c9a6e4e7dca2
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Linked notes

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