Acetic Acid → 1-benzyl-N-methylpiperidin-4-amine

HRID 1193388Notes

Reaction equation

HRID 1193388 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=O.CN.Cl.[BH3-][C:23]#[N:24].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:24][CH3:23])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 192201-Benzyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 41361281-benzyl-N-methylpiperidin-4-amineYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzylpiperidin-4-one (5.0 g, 26.315 mmol, 1.0 eq.) was dissolved in MeOH (78 ml); AcOH (0.2 ml) and CH3NH2.HCl (2.6 g, 39.47 mmol, 1.5 eq.) were added and stirring was carried out for 2 hours at RT. NaCNBH3 (3.3 g, 52.63 mmol, 2.0 eq.) was then added in portions at 0° C. and the mixture was stirred for 16 hours at RT. The reaction mixture was concentrated under reduced pressure. The residue was taken up in sat. sodium hydrogen carbonate solution (150 ml) and extracted with DCM (2×200 ml). The combined org. phases were dried over sodium sulfate, concentrated and used in the next stage without being purified further. Yield: 92% (5.0 g, 24.509 mmol)

Workup

  1. stirringthe mixture was stirred for 16 hours at RT
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with DCM (2×200 ml)
  4. dry with materialphases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customwithout being purified further

Sources & evidence

ORD record
ord-acd6e5ce947740caa3e151862205295d
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…