Acetic Acid → N-Butyl-N-[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amine

HRID 1269613Notes

Reaction equation

HRID 1269613 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.[CH:19](=O)[CH2:20][CH2:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:19]([NH:8][C:7]1[C:2]([CH3:1])=[C:3]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=2)[CH:4]=[CH:5][CH:6]=1)[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 5049666Sodium triacetoxyborohydrideHCID 184483532-Methyl-4'-(trifluoromethyl)biphenyl-3-amine

Product 1

HCID 18448423N-Butyl-N-[2-methyl-4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4′-(trifluoromethyl)-1,1′-biphenyl-3-ylamine (0.32 g, 1.26 mmol) in anhydrous CH2Cl2 (10 mL) under nitrogen at room temperature was added butyraldehyde (0.114 mL, 1.26 mmol), followed 10 min later by sodium triacetoxyborohydride (0.374 g, 1.76 mmol) and acetic acid (72 μL, 1.26 mmol). The resultant mixture was stirred for 22 h at room temperature. The reaction mixture was quenched with sat. NaHCO3 aq. (15 mL), then extracted with CH2Cl2 (2×20 mL). The organic solution was passed through a hydrophobic frit and the solvent was removed in vacuo. Purification by SPE (20 g Silica cartridge) eluted with 1:200 EtOAc:cyclohexane afforded the title compound as a colourless oil (221 mg).

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3 aq. (15 mL)
  2. extractionextracted with CH2Cl2 (2×20 mL)
  3. customthe solvent was removed in vacuo
  4. customPurification by SPE (20 g Silica cartridge)
  5. washeluted with 1:200 EtOAc

Sources & evidence

ORD record
ord-7e337745ab804fb591a442adb5f7254e
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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