Epichlorohydrin → 3-[(S)-[(3-chloro-2-hydroxypropyl)amino](4-chlorophenyl)methyl]benzonitrile

HRID 1724172Notes

Reaction equation

HRID 1724172 reaction equation
[NH2:1][C@@H:2]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[CH2:18]([CH:20]1[O:22][CH2:21]1)[Cl:19]>CO>[Cl:19][CH2:18][CH:20]([OH:22])[CH2:21][NH:1][C@@H:2]([C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 670553723-[(s)-Amino(4-chlorophenyl)methyl]benzonitrile

Product 1

HCID 670553403-[(S)-[(3-chloro-2-hydroxypropyl)amino](4-chlorophenyl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14.0 g (58 mmole) of 3-[(S)-amino(4-chlorophenyl)methyl]benzonitrile and 10.8 g (120 mmole) of epichlorhydrin in 200 mL of methanol was stirred in the dark for 72 hours. The solution was partitioned between CH2Cl2 and water and the layers were separated. The organic layer was dried over Na2SO4 and concentrated to afford the title compound, which was used in the next step without purification; 335 (M+1, 35Cl); 337 (M+1, 37Cl).

Workup

  1. customThe solution was partitioned between CH2Cl2 and water
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b53f6c28bbd4da393b7106d0705da3a
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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