HCID 12151021, compound → 4-Benzylpiperidine-4-carboxylic acid methylamide

HRID 380658Notes

Reaction equation

HRID 380658 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:14](=[O:17])[NH:15][CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:16][NH:15][C:14]([C:11]1([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:17]

Participants

4

Reactant 1

HCID 12151021HCID 12151021, compound

Product 1

HCID 121510224-Benzylpiperidine-4-carboxylic acid methylamideYield 76.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-Benzyl-4-methylcarbamoylpiperidine-1-carboxylic acid tert-butyl ester (2.8 g) was dissolved in a mixture of TFA and methylene chloride and stirred for 40 min. The solvent was removed in vacuo and the residue was dissolved in water (30 ml) and pH was adjusted to 13 with aqueous sodium hydroxide (1N). The aqueous phase was extracted with methylene chloride (3×75 ml) and the combined organic phases were dried (MgSO4) and evaporated in vacuo to afford 1.50 g of 4-benzylpiperidine-4-carboxylic acid methylamide.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (30 ml)
  3. extractionThe aqueous phase was extracted with methylene chloride (3×75 ml)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-562f52bc546c438dbb6f91d108f795b2
Source dataset
uspto-grants-2001_10
Patent number
US06303620B1

Reaction notes

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