Triethylamine → HCID 25179430, compound

HRID 2101262Notes

Reaction equation

HRID 2101262 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.[F:14][C:15]([F:27])([F:26])[O:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][NH2:25])[CH:20]=[CH:21][CH:22]=1.C(N(CC)CC)C.[BH4-].[Na+]>CO.O>[F:14][C:15]([F:26])([F:27])[O:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][NH:25][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:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 6375734-(Trimethylsilyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 574385032-[3-(Trifluoromethoxy)phenyl]ethan-1-amine hydrochloride

Product 1

HCID 25179430HCID 25179430, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Trimethylsilanyl-benzaldehyde (178 mg, 1 mmol), 2-(3-trifluoromethoxy-phenyl)-ethyl-amine hydrochloride (241 mg, 1.1 mmol) and triethyl amine (151 mg, 1.5 mmol) were dissolved in methanol (5 ml) and the solution was stirred at rt for 5 min. Sodium borohydride (37 mg, 1 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 off and concentrated in vacuo to yield [2-(3-trifluoromethoxy-phenyl)-ethyl]-(4-trimethylsilanyl-benzyl)-amine (370 mg, 100%) as a colorless oil. MS (ISP) 368.2 (100) (M+H)+.

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 off
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fce47b64154467ebe06bb2fd9e7f25d
Source dataset
uspto-grants-2009_08
Patent number
US07572823B2

Reaction notes

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