Benzaldehyde → 2-(Benzylamino)-2-methylpropan-1-ol

HRID 584239

Reaction equation

HRID 584239 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.O.C(O)(=O)C>[CH2:7]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 118072-Amino-2-methyl-1-propanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 9623682-(Benzylamino)-2-methylpropan-1-olYield 78.1%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Acetic acid (5.4 ml) was added to a solution of 2-amino-2-methyl-1-propanol (8.4 g) and benzaldehyde (10 g) in 1,2-dichloroethane (140 ml) under ice-cooling. After 30 minutes of stirring at the same temperature, sodium triacetoxyborohydride (26 g) was added by small portions to the solution over 10 minutes. After 2 hours of stirring at room temperature, the mixture was poured into a solution of sodium hydrogen carbonate (48 g) in water (300 ml). The aqueous layer was separated and adjusted to pH 12 with 24% sodium hydroxide aqueous solution. The alkaline solution was extracted with ethyl acetate (2 times). The extract was dried over sodium sulfate and evaporated under reduced pressure to give colorless crystals of 2-benzylamino-2-methyl-1-propanol (13.2 g).

Workup

  1. temperaturecooling
  2. additionwas added by small portions to the solution over 10 minutes
  3. customThe aqueous layer was separated
  4. extractionThe alkaline solution was extracted with ethyl acetate (2 times)
  5. dry with materialThe extract was dried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bd9fd6a8d6ba447c9c58946ab8d61e95
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Linked notes

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