Hydrochloric Acid → (2-Chloro-4-cyclopropyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

HRID 855340Notes

Reaction equation

HRID 855340 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH:10]2[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:9]=[C:8]([CH:10]2[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[CH2:4][NH:23][CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:24])[F:25])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 104223Phenethylamine, m-trifluoromethyl-HCID 4311764Sodium borohydrideHCID 860937372-Chloro-4-cyclopropylbenzaldehyde

Product 1

HCID 69342626(2-Chloro-4-cyclopropyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.927 g of 2-chloro-4-cyclopropyl-benzaldehyde (5.37 mmol) and 1.52 g 2-(3-trifluoromethyl-phenyl)-ethylamine (8.05 mmol) were dissolved in 15 ml methanol and refluxed for 2 h. After cooling down to rt, the reaction mixture was treated in portions with 305 mg NaBH4, stirred at rt for 10 min and 12 h under reflux. The reaction mixture was then cooled to rt, treated with 1 ml 1N HCl and concentrated in vacuo. The resulting oil was then diluted with EtOAc, washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (40 g silicagel, heltane/AcOEt 2:1) leading to 1.41 g (2-chloro-4-cyclopropyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine (74%) as a yellow oil. MS: 354 (M+H)+.

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was then cooled to rt
  4. concentrationconcentrated in vacuo
  5. additionThe resulting oil was then diluted with EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography (40 g silicagel, heltane/AcOEt 2:1)

Sources & evidence

ORD record
ord-b60a108384ce4aa29138fc659eba63ed
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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