4-tert-Butylbenzaldehyde → [Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine

HRID 855207

Reaction equation

HRID 855207 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:13][CH2:14][CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[OH:16].[BH4-].[Na+]>CO.O.CCOC(C)=O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 703244-tert-ButylbenzaldehydeHCID 4124342-Amino-1-(4-chlorophenyl)ethan-1-olHCID 4311764Sodium borohydride

Product 1

HCID 69342320[Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

1 ml of 4-tert-butylbenzaldehyde (6.15 mmol) and 960 mg of [rac]-2-amino-1-(4-chloro -phenyl)-ethanol (estimated 4.1 mmol) were dissolved in 40 ml methanol at rt, and after stirring for 5 min at rt, were refluxed for 2 h. After cooling down to rt, 310 mg (8.2 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was then refluxed for 2 h. After cooling down to rt, the residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was stirred with a small quantity of diethylether/heptane, filtered and the solid dried under high vacuo, leading to 723 g of [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine as a white solid (55%). MS (ISP) 318.2 (M+H)+.

Workup

  1. temperaturewere refluxed for 2 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 15 min at rt
  4. temperaturethe reaction mixture was then refluxed for 2 h
  5. temperatureAfter cooling down to rt
  6. customAfter separation of the organic phase
  7. extractionthe aqueous phase was extracted with EtOAc
  8. washthe combined organic phases were washed with brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered off
  11. concentrationconcentrated in vacuo
  12. stirringThe residue was stirred with a small quantity of diethylether/heptane
  13. filtrationfiltered
  14. customthe solid dried under high vacuo

Sources & evidence

ORD record
ord-639939a6e94546d8a4bbb53f9d41552b
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Linked notes

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