Water → 4-[2-[(3-Chloro-beta-hydroxyphenethyl)amino]propyl] phenoxyacetonitrile

HRID 465442Notes

Reaction equation

HRID 465442 reaction equation
C(=O)(O)O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]([OH:15])[CH2:13][NH2:14])[CH:9]=[CH:10][CH:11]=1.[CH2:16]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][C:26]#[N:27])=[CH:22][CH:21]=1)[C:17]([CH3:19])=O.O>C1C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH:12]([OH:15])[CH2:13][NH:14][CH:17]([CH3:19])[CH2:16][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][C:26]#[N:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 198745284-AcetonylphenoxyacetonitrileHCID 678659382-(3-Chlorophenyl)-2-hydroxyethylamine carbonate

Product 1

HCID 198745234-[2-[(3-Chloro-beta-hydroxyphenethyl)amino]propyl] phenoxyacetonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-(3-chlorophenyl)-2-hydroxyethylamine carbonate (3.35 g) and 4-acetonylphenoxyacetonitrile in benzene was heated under reflux for 1 h with azeotropic removal of water using a Dean and Stark head. The solution was cooled, and the solvent removed in vacuo. The residue was dissolved in methanol and treated with sodium cyanoborohydride (1.25 g) and stirred for 5 h at ambient temperature. The solvent was then evaporated under reduced pressure, the residue dissolved in ethyl acetate, washed with water (2×50 ml), brine (1×50 ml), dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography on silica using methanol:chloroform 2:98 as eluent to give 4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl] phenoxyacetonitrile, (4.0 g).

Workup

  1. temperaturewas heated
  2. temperatureThe solution was cooled
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in methanol
  5. additiontreated with sodium cyanoborohydride (1.25 g)
  6. customThe solvent was then evaporated under reduced pressure
  7. dissolutionthe residue dissolved in ethyl acetate
  8. washwashed with water (2×50 ml), brine (1×50 ml)
  9. dry with materialdried (magnesium sulphate)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-4ff91e93c4174e56ba8d32880a7ba7a9
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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