Benzene → 2-{2-[4-(3-Hydroxypropyl) phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl) ethanol

HRID 1901152Notes

Reaction equation

HRID 1901152 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:28])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](OC)=[O:25])=[CH:18][CH:17]=1.C1C=CC=CC=1.[BH4-].[Na+]>CO>[OH:25][CH2:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:13]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[OH:4])[CH3:28])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 4311764Sodium borohydrideHCID 21832185Methyl 3-[4-(2-oxopropoxy)phenyl]propionate

Product 1

HCID 218321372-{2-[4-(3-Hydroxypropyl) phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl) ethanolYield 53.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 2 was repeated, except that 4.3 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 3.5 g of methyl 3-[4-(2-oxopropoxy)phenyl]propionate (prepared as described in Preparation 5), 150 ml of benzene, 150 ml of absolute methanol and 6.12 g of sodium borohydride were used. A crude product was obtained, and this was purified by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the eluent, to give 2.9 g of the title compound having an Rf=0.40 (thin layer chromatography over silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the developing solvent).

Workup

  1. customA crude product was obtained
  2. customthis was purified by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and ethanol as the eluent

Sources & evidence

ORD record
ord-13ab0e3673124d1f9179c9a260ad7540
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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