Ammonium Hydroxide → 3-Amino-1-phenylpropan-1-ol

HRID 1182784Notes

Reaction equation

HRID 1182784 reaction equation
[C:1]1([CH:7]([OH:15])[CH2:8][CH2:9]CS([O-])(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+:17]>O1CCCC1>[NH2:17][CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:15]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 231125733-Phenyl-3-hydroxypropylmethanesulfonate

Product 1

HCID 1215483-Amino-1-phenylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-phenyl-3-hydroxypropylmethanesulfonate (1.71 g, Gao, et al., J. Org. Chem., 1988, 53, 4081), tetrahydrofuran (10 mL) and 28% ammonium hydroxide (30 mL) was heated in a bomb at 65° C. for 16 hours. After cooling, the volatiles were eliminated to leave the aqueous solution which was extracted with ether. The aqueous layer was concentrated under reduced pressure, azeotroped twice with anhydrous acetonitrile and dried under vacuum to give 3-amino-1-phenyl-1-propanol (1.04 g) as a white solid: mp 92-94° C., Rf=0.1 (silica, methanol/ethyl acetate 1/1).

Workup

  1. temperatureAfter cooling
  2. customto leave the aqueous solution which
  3. extractionwas extracted with ether
  4. concentrationThe aqueous layer was concentrated under reduced pressure
  5. customazeotroped twice with anhydrous acetonitrile
  6. customdried under vacuum

Sources & evidence

ORD record
ord-39c7de63d4b24bc9bb5d85b345118a53
Source dataset
uspto-grants-2014_03
Patent number
US08664195B2

Reaction notes

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