Hydrochloric Acid → N,N-dimethyl-1-[(2S)-2-piperidinyl]methanamine hydrochloride

HRID 1366702Notes

Reaction equation

HRID 1366702 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1CC1C=CC=CC=1.[ClH:18]>CO>[ClH:18].[CH3:1][N:2]([CH3:17])[CH2:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66936277N,N-dimethyl-1-[(2S)-1-(phenylmethyl)-2-piperidinyl]methanamine

Product 1

HCID 66936423N,N-dimethyl-1-[(2S)-2-piperidinyl]methanamine hydrochlorideYield 93.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N-Dimethyl-1-[(2S)-1-(phenylmethyl)-2-piperidinyl]methanamine (590 mg, 2.539 mmol) was dissolved in a mixture of MeOH (20 mL) and 1N HCl (5.5 mL, 5.5 mmol), degassed and placed under argon. 10% Pd/C (117 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 N,N-dimethyl-1-[(2S)-2-piperidinyl]methanamine hydrochloride (425 mg, 78%). LCMS: (M+H)+: not detected.

Workup

  1. customdegassed
  2. addition10% Pd/C (117 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-446f5f039fde45bc87ba9a6712ce5dc6
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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