Acetic Acid → 1-Benzyl-3,3-diMethyl-piperidin-4-aMine

HRID 1694292Notes

Reaction equation

HRID 1694292 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10]([CH3:16])([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.CO.[BH4-].[Na+].[NH3:25]>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:25])[C:10]([CH3:16])([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 887MethanolHCID 4311764Sodium borohydrideHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 102361061-Benzyl-3,3-diMethyl-piperidin-4-aMine

Procedure

A solution of 1-benzyl-3,3-dimethylpiperidin-4-one (900 mg, 4.14 mmol) and acetic acid (474 μl, 8.28 mmol) in 7 M NH3 in MeOH (35.5 ml, 249 mmol) was first stirred for 30 min at RT. Then NaBH4 (1.57 g, 41.4 mmol) was added at RT. The reaction batch was stirred for 30 min at RT, concentrated and then diluted with DCM (100 ml). The organic phase was washed with saturated aqueous NaHCO3, dried and concentrated to dryness.

Workup

  1. concentrationconcentrated
  2. additiondiluted with DCM (100 ml)
  3. washThe organic phase was washed with saturated aqueous NaHCO3
  4. customdried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5af433e9203940c283f3d0e5efd18575
Source dataset
uspto-grants-2012_04
Patent number
US08158628B2

Reaction notes

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