Water → 5-Chloro-alpha-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol

HRID 1772

Reaction equation

HRID 1772 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH:22]=O.[BH4-].[Na+].O>C(O)(=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:20]=2[O:19][CH3:18])=[C:3]([CH:13]=1)[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11]

Participants

6

Reactant 4

HCID 962WaterHCID 691752,4-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 11437092(2-Amino-5-chlorophenyl)(2-chlorophenyl)methanol

Product 1

HCID 538414955-Chloro-alpha-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcoholYield 96.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction with ethyl acetate (200 ml×2). The ethyl acetate layer was washed with 1N sodium hydroxide, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol (7.5 g) as an oily product.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  3. washThe ethyl acetate layer was washed with 1N sodium hydroxide, which
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8208d819f879448fbecf7d2aa5f1ad04
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

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