Water → HCID 19874503, compound

HRID 465425Notes

Reaction equation

HRID 465425 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([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:3][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>C1C=CC=CC=1>[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:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:10][CH:11]=2)[OH:19])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 19874572HCID 19874572, compound

Product 1

HCID 19874503HCID 19874503, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-[4-(4-pyridylmethyloxy)phenyl)propan-2-one (2.5 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (1.78 g) in benzene (100 ml) 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 (1.0 g). After stirring for 1 hour the methanol was evaporated, the residue partitioned between ethyl acetate and water, the washed organic phase dried and evaporated to give an oil which was chromatographed on Kieselgel 60. Elution with 4% methanol in chloroform gave 3-chloro-α-[[[2-[4-[4-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol m.p. 85°-110° C. (ethylacetate-ether) as a 45:55 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 (1.0 g)
  5. customwas evaporated
  6. customthe residue partitioned between ethyl acetate and water
  7. customthe washed organic phase dried
  8. customevaporated
  9. customto give an oil which
  10. customwas chromatographed on Kieselgel 60
  11. washElution with 4% methanol in chloroform

Sources & evidence

ORD record
ord-2cba99f8d03b459190815887094c43bb
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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