Benzylamine → 1-Benzylamino-2-cyano-3-hydroxypentane

HRID 1975482Notes

Reaction equation

HRID 1975482 reaction equation
[C:1]([C:3]([CH:5]([OH:8])[CH2:6][CH3:7])=[CH2:4])#[N:2].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[CH2:9]([NH:16][CH2:4][CH:3]([C:1]#[N:2])[CH:5]([OH:8])[CH2:6][CH3:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 110623372-(1-Hydroxypropyl)acrylonitrile

Product 1

HCID 190993201-Benzylamino-2-cyano-3-hydroxypentane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-cyano-3-hydroxy-1-pentene (10 g) in methanol (100 ml) was added benzylamine (10 ml). After stirring for 8 hours under reflux, the solvent was evaporated, and the residue was chromatographed on silica gel with eluting a mixture of n-hexane and ethyl acetate (1:1, V/V) to give 1-benzylamino-2-cyano-3-hydroxypentane (10 g).

Workup

  1. temperatureunder reflux
  2. customthe solvent was evaporated
  3. customthe residue was chromatographed on silica gel
  4. washwith eluting
  5. additiona mixture of n-hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-c07ccba7fd5943e88fa02572e3131f4b
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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