Acetic Acid → HCID 58531607, compound

HRID 1889692Notes

Reaction equation

HRID 1889692 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[CH:23][CH:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:7][C:6]3[CH:16]=[CH:17][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=3)=[CH:9][CH:10]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 673264-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 133008444-(4-(Trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 58531607HCID 58531607, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 4-(4-(trifluoromethyl)phenoxy)benzaldehyde (1.4 g, 5.2 mmol) in anhydrous dichloroethane (10 mL), at room temperature under nitrogen, was added (4-fluorophenyl)methanamine (0.6 mL, 52 mmol). The mixture was stirred for 3 minutes before acetic acid (0.42 mL, 7.3 mmol) was added dropwise via syringe. After an additional 30 minutes, sodium triacetoxyborohydride (1.6 g, 7.3 mmol) was added to the reaction mixture. After 20 h, the reaction was quenched with 1 N aqueous NaOH (30 mL) then extracted with chloroform. The organic extracts were combined, washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (ISCO system, eluting with 0-5% MeOH in CHCl3) to afford the desired compound (0.51 g, 24%) as a colorless oil. MS (ESI): 376.1 (M+H)+.

Workup

  1. additionwas added dropwise via syringe
  2. waitAfter 20 h
  3. customthe reaction was quenched with 1 N aqueous NaOH (30 mL)
  4. extractionthen extracted with chloroform
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel flash chromatography (ISCO system, eluting with 0-5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-938928b83780493293009d38d2367976
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

Loading…