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

HRID 1269602Notes

Reaction equation

HRID 1269602 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:5][CH:4]=1.[CH:18](=O)[CH2:19][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>[CH2:18]([NH:15][C:11]1[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:16])([F:17])[F:1])=[CH:8][CH:7]=2)[CH:14]=[CH:13][CH:12]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8063PentanalHCID 27827084'-(Trifluoromethyl)-[1,1'-biphenyl]-3-amineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18448425N-Pentyl-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4′-(trifluoromethyl)-1,1′-biphenyl-3-ylamine (0.3 g, 1.26 mmol) in anhydrous CH2Cl2 (10 mL) under nitrogen at room temperature was added valeraldehyde (0.134 mL, 1.26 mmol), sodium triacetoxyborohydride (0.374 g, 1.76 mmol) and acetic acid (72 μl, 1.26 mmol). The resultant mixture was stirred for 17 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 dried (Na2SO4) and the solvent was removed in vacuo. Purification by SPE (20 g Silica column) eluted with 1:200 EtOAc:cyclohexane afforded the title compound as a colourless oil (0.17 g).

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3 aq. (15 mL)
  2. extractionextracted with CH2Cl2 (2×20 mL)
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customPurification by SPE (20 g Silica column)
  6. washeluted with 1:200 EtOAc

Sources & evidence

ORD record
ord-f2d85215920c4a6aab57ab877bc6c10f
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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