Water → [2-(3,4-Dichloro-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amine

HRID 2101264Notes

Reaction equation

HRID 2101264 reaction equation
[CH3:1][Si:2]([CH3:12])([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][NH2:23])[CH:17]=[CH:18][C:19]=1[Cl:20].[BH4-].[Na+].O>CO>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][NH:23][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([Si:2]([CH3:12])([CH3:11])[CH3:1])=[CH:4][CH:5]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

6

Reactant 4

HCID 962WaterHCID 2179583,4-DichlorophenethylamineHCID 6375734-(Trimethylsilyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 57438504[2-(3,4-Dichloro-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amineYield 103.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Trimethylsilanyl-benzaldehyde (800 mg, 4.5 mmol) and 2-(3,4-dichloro-phenyl)-ethylamine (1023 mg, 5.4 mmol) were dissolved in methanol (5 ml) and the solution was stirred at rt for 5 min. Sodium borohydride (166 mg, 4.5 mmol) was added under nitrogen and the reaction mixture was stirred at rt for 1 h. Water was added and methanol was evaporated in vacuo. The reaction was extracted twice with diethyl ether and the combined organic layers were washed once with water and once with sat. aq. NaCl solution, dried with sodium sulfate, filtered and concentrated in vacuo to yield [2-(3,4-dichloro-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amine (1640 mg, 100%) as a colorless oil. MS (ISP): 352.2/354.2 (100/74) (M+H)+. 1HNMR (CDCl3, 300 MHz): δ 7.48 (d, 2H), 7.25-7.35 (m, 4H), 7.02 (dd, 2H), 3.79 (s, 2H), 2.75-3.00 (m, 4H), 0.26 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred at rt for 1 h
  2. custommethanol was evaporated in vacuo
  3. extractionThe reaction was extracted twice with diethyl ether
  4. washthe combined organic layers were washed once with water and once with sat. aq. NaCl solution
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-342c80a2283645a7b8b8ec7fa3dff3c7
Source dataset
uspto-grants-2009_08
Patent number
US07572823B2

Reaction notes

Loading…