Hydrochloric Acid → (2S)-N,N-dimethyl-2-piperidinecarboxamide hydrochloride

HRID 1366699Notes

Reaction equation

HRID 1366699 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1C(OCC1C=CC=CC=1)=O)=[O:4].[ClH:22]>CO>[ClH:22].[CH3:1][N:2]([CH3:21])[C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66936339phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylate

Product 1

HCID 66936649(2S)-N,N-dimethyl-2-piperidinecarboxamide hydrochlorideYield 116.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylate (1.918 g, 6.609 mmol) was dissolved in a mixture of MeOH (40 mL) and 1N HCl (14.53 mL, 14.53 mmol), degassed and placed under argon. 10% Pd/C (575 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for 2 h. The contents were then degassed, and the Pd/C was removed by filtration through a fiberglass filter, washing with MeOH. The filtrate was concentrated in vacuo to provide pure (2S)—N,N-dimethyl-2-piperidinecarboxamide hydrochloride (1.483 g, >99%). LCMS: (M+H)+: 157.2.

Workup

  1. customdegassed
  2. addition10% Pd/C (575 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor 2 h
  5. customThe contents were then degassed
  6. customthe Pd/C was removed by filtration through a fiberglass
  7. filtrationfilter
  8. washwashing with MeOH
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-899d104a8aea42b98538e3f1141dbc6a
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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