Water → (2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amine

HRID 902682Notes

Reaction equation

HRID 902682 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([CH3:9])[CH:7]=O.[Cl:10][C:11]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl.CCCCCC>[Cl:10][C:11]1[C:18]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH:14][CH2:7][CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 110517432-(Thiophen-2-yl)propanal

Product 1

HCID 69253724(2-Chloro-3-trifluoromethyl-benzyl)-(2-thiophen-2-yl-propyl)-amineYield 107%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-thiophen-2-yl-propionaldehyde (100 mg, 0.7 mmol) in dry dichloromethane (20 ml) was added 2-chloro-3-trifluoromethyl-benzylamine (30 mg, 0.14 mmol) followed by the addition of sodium triacetoxyborohydride (60.5 mg, 0.28 mmol). After the resulting mixture was stirred at room temperature overnight water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by silica gel column chromatograph using EtOAc:Hexane/25:75 as the eluent to give 50 mg (40% yield) of the title compound as an oil. MS m/e 334.4 (M+H)+.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacco
  8. customThe crude mixture was purified by silica gel column chromatograph

Sources & evidence

ORD record
ord-8ee8eb59e042489ea95fc8c016eb9639
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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