Hydrochloric Acid → [2-(3-Benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amine

HRID 855183Notes

Reaction equation

HRID 855183 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].Cl.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][NH2:30])[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].Cl>CO>[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][NH:30][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 703244-tert-ButylbenzaldehydeHCID 207414Benzeneethanamine, 3-(phenylmethoxy)-, hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 68562248[2-(3-Benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.52 ml of 4-tert-butylbenzaldehyde (9.1 mmol) and 1.6 g 2-(3-benzyloxy-phenyl)-ethylamine hydrochloride (6.07 mmol) and 838 mg potassium carbonate (6.07 mmol) were suspended in 18 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2 h. After cooling down to rt, 344 mg (9.1 mmol) sodium borohydride were added and after stirring for 5 min at rt, the reaction mixture was then refluxed for 2.5 h. After cooling down to rt, the reaction mixture was treated with 2 ml 1 N HCl and concentrated in vacuo. 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 purified by column chromatography (40 g silica gel; EtOAc/heptane 1:1) to give 2.13 g [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amine as a light yellow viscous oil (94%). MS (ISP) 374.5 (M+H)+.

Workup

  1. temperaturewere refluxed for 2 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 5 min at rt
  4. temperaturethe reaction mixture was then refluxed for 2.5 h
  5. temperatureAfter cooling down to rt
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with water/EtOAc
  8. customAfter separation of the organic phase
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered off
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:1)

Sources & evidence

ORD record
ord-faf03e60af434ca29d8d0c7de1ecfa6d
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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