Sodium Hydroxide → HCID 67017771, compound

HRID 2243170Notes

Reaction equation

HRID 2243170 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][CH2:21][NH2:22])[CH:16]=[CH:17][C:18]=1[Cl:19].[BH4-].[Na+].[OH-].[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][NH:22][CH2:21][CH2:20][C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 613412-BenzofurancarboxaldehydeHCID 2179583,4-DichlorophenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 67017771HCID 67017771, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 150 mg (1.03 mmol) of benzofuran-2-carbaldehyde and 195 mg (1.03 mmol) of 2-(3,4-dichloro-phenyl)-ethylamine in methanol (4 ml) was heated to reflux for 3 h. Then the reaction mixture was allowed to cool to RT and 58 mg (1.54 mmol) of sodium borohydride were added. The mixture was heated to reflux over night. After cooling to RT, 0.1 N sodium hydroxide solution was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography (silica gel; dichloromethane and dichloromethane/methanol 95:5). The title compound was isolated as yellow oil (249 mg, 76%). MS (ISP) 320.2 (M+H)+.

Workup

  1. temperatureto reflux for 3 h
  2. temperatureThe mixture was heated
  3. temperatureto reflux over night
  4. temperatureAfter cooling to RT
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel; dichloromethane and dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-84b1ccfe35d247e0ba3eb43a608e36f3
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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