2-Amino-1-(3-chlorophenyl)ethan-1-ol → 3-Chloro-alpha-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol

HRID 465424Notes

Reaction equation

HRID 465424 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](=O)[CH3:17])=[CH:11][CH:10]=2)[CH:2]=1.[OH:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)[CH2:21][NH2:22]>O>[Cl:29][C:25]1[CH:24]=[C:23]([CH:20]([CH2:21][NH:22][CH:16]([CH3:17])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:10][CH:11]=2)[OH:19])[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 19874530[4-(3-Pyridylmethyloxy)phenyl]propan-2-one

Product 1

HCID 198745693-Chloro-alpha-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanolYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-[4-(3-pyridylmethyloxy)phenyl]propan-2-one (7.2 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (5.1 g) was boiled under reflux with azeotropic removal of water until the reaction was complete. The solvent was evaporated, the residue dissolved in methanol (150 ml), cooled in an ice-bath and treated with sodium borohydride (5 g). After stirring for 1 hour the methanol was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried and evaporated to give an oil which was chromatographed on Kieselgel 60. Elution with 3% methanol in chloroform gave a yellow oil (6.4 g). Bulb to bulb distillation of this oil gave 3-chloro-β-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol b.p. 120°-130° C./0.4 mm, as a 1:1 mixture of diastereoisomers.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol (150 ml)
  3. temperaturecooled in an ice-bath
  4. additiontreated with sodium borohydride (5 g)
  5. customwas evaporated
  6. customthe residue partitioned between ethyl acetate and water
  7. washThe organic phase was washed with water
  8. customdried
  9. customevaporated
  10. customto give an oil which
  11. customwas chromatographed on Kieselgel 60
  12. washElution with 3% methanol in chloroform

Sources & evidence

ORD record
ord-2a926d5b8195484bbad19fff3e7c2b87
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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