Hydrochloric Acid → N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-methoxybenzeneethanamine

HRID 855226Notes

Reaction equation

HRID 855226 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].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1.[BH4-].[Na+].Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 703244-tert-ButylbenzaldehydeHCID 748663-MethoxyphenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 39418093N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-methoxybenzeneethanamineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.22 ml of 2-(3-methoxy-phenyl)-ethylamine (1.5 mmol) were dissolved in 5 ml methanol at rt and then refluxed for 2 h. After cooling down to rt, 85 mg (2.25 mmol) of sodium borohydride were added in portions and the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 0.15 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 (90 g silica gel; EtOAc/heptane 1:1) to give 520 mg light yellow oil (>100%).

Workup

  1. temperaturerefluxed for 2 h
  2. temperaturethe reaction mixture was then refluxed for 3 h
  3. temperatureAfter cooling down to rt
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with water/EtOAc
  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. customThe residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:1)

Sources & evidence

ORD record
ord-9e2d3240f3a345eea89d34dffa681b9f
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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