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

HRID 1269600Notes

Reaction equation

HRID 1269600 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[F:6][C:7]([F:22])([F:21])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)=[CH:10][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:1]([NH:20][C:16]1[CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([F:6])([F:21])[F:22])=[CH:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 27827084'-(Trifluoromethyl)-[1,1'-biphenyl]-3-amineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18448424N-Butyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of butyraldehyde (0.114 mL, 1.26 mmol) in anhydrous CH2Cl2 under nitrogen, was added 4′-(trifluoromethyl)-1,1′-biphenyl-3-ylamine (0.3 g, 1.26 mmol). After 15 mins sodium triacetoxyborohydride (0.375 g, 1.77 mmol) was added portion wise, followed by acetic acid (0.072 mL, 1.26 mmol). After stirring the mixture for 18 h the reaction was quenched by cautious addition of sat. sodium bicarbonate aq. (20 mL) and extracted with CH2Cl2 (2×30 mL). The organic extract was separated by hydrophobic frit and the solvents removed in vacuo. Purification by SPE (Silica, 10 g) eluting with 99:1 cyclohexane:EtOAc, afforded the title compound as a colourless oil (0.25 g).

Workup

  1. customwas quenched by cautious addition of sat. sodium bicarbonate aq. (20 mL)
  2. extractionextracted with CH2Cl2 (2×30 mL)
  3. extractionThe organic extract
  4. customwas separated by hydrophobic frit
  5. customthe solvents removed in vacuo
  6. customPurification by SPE (Silica, 10 g)
  7. washeluting with 99:1 cyclohexane

Sources & evidence

ORD record
ord-3e18c9aa647442bcbc92df1e943c82a2
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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