1-[Benzyl(methyl)amino]propan-2-one → 1-[Benzyl(methyl)amino]propan-2-ol

HRID 1926894Notes

Reaction equation

HRID 1926894 reaction equation
[CH2:1]([N:8]([CH3:13])[CH2:9][C:10]([CH3:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]([CH3:13])[CH2:9][CH:10]([OH:11])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5200831-[Benzyl(methyl)amino]propan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 2326191-[Benzyl(methyl)amino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Put 8.00 g (45.13 mmol) 1-[benzyl(methyl)amino]acetone in 40 ml methanol. Add, at RT in portions with stirring, 854 mg (22.57 mmol) sodium borohydride. Stir for 30 min at RT and then for a further 30 min under reflux. Concentrate by evaporation and take up the residue in water. Extract twice with ethyl acetate, wash the combined organic phases once with satd. sodium hydrogencarbonate solution, dry over magnesium sulphate and concentrate by evaporation. 7.80 g (81.9% of theor.) of the target compound is obtained without further purification.

Workup

  1. additionAdd, at RT in portions
  2. stirringStir for 30 min at RT
  3. temperaturefor a further 30 min under reflux
  4. concentrationConcentrate by evaporation
  5. extractionExtract twice with ethyl acetate
  6. washwash the combined organic phases once with satd
  7. dry with materialsodium hydrogencarbonate solution, dry over magnesium sulphate
  8. concentrationconcentrate by evaporation
  9. custom7.80 g (81.9% of theor.) of the target compound is obtained without further purification

Sources & evidence

ORD record
ord-195130dbb46142f79a892853d38fde5c
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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