Acetic Acid → HCID 58531372, compound

HRID 1889688Notes

Reaction equation

HRID 1889688 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=2)=[CH:13][CH:12]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:18]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 673264-Fluorobenzylamine2×HCID 13942383-(4-Chlorophenyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58531372HCID 58531372, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a homogeneous mixture of (4-fluorophenyl)methanamine (2.5 mL, 21.8 mmol) and 4′-chlorobiphenyl-3-carbaldehyde (Aldrich, 3.6 g, 16.8 mmol) in anhydrous dichloroethane (25 mL), under nitrogen atmosphere, was added acetic acid (1.2 mL, 21.0 mmol). The mixture was stirred at room temperature for 13.5 h before sodium triacetoxyborohydride (5.0 g, 23.5 mmol) was added. After 4 h, (4-fluorophenyl)methanamine (2.5 mL, 21.8 mmol) was added and the stirring continued. After an additional 5 h of stirring, the reaction was quenched with 1 N aq. NaOH solution (50 mL) then extracted twice 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 (Merck KGaA, 230-400 mesh particle size) eluting with 0-70% ethyl acetate in hexane, to afford the title compound (3.43 g, 59%) as a colorless oil. MS (ESI): 326.1 (M+H)+.

Workup

  1. additionwas added
  2. customthe reaction was quenched with 1 N aq. NaOH solution (50 mL)
  3. extractionthen extracted twice with chloroform
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography (Merck KGaA, 230-400 mesh particle size)
  9. washeluting with 0-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0b7c915ef6c34d6ca8929ef09376ce51
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

Loading…