Acetic Acid → HCID 28531147, compound

HRID 1725244Notes

Reaction equation

HRID 1725244 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)([CH3:12])[CH3:11].C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([CH:10]([CH3:12])[CH3:11])=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 326CuminaldehydeHCID 660364-ChlorobenzylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 28531147HCID 28531147, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-chlorobenzylamine (2.83 g, 20.0 mmol) and 4-isopropylbenzaldehyde (2.96 g, 20.0 mmol) in methanol (100 mL) were added acetic acid (4.6 mL, 80 mmol) and sodium cyanoborohydride (1.51 g, 24.0 mmol) and the solution was stirred at room temperature for three days. Water (5 mL) was added and the mixture was concentrated in vacuo. The residue was taken up in ethyl acetate (100 mL) and aqueous 1 M KOH (100 mL) and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×100 mL) and the combined organic phase was washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 5.80 g of crude product as a white semicrystalline oil. The product was used in the subsequent reaction step without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customaqueous 1 M KOH (100 mL) and the phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL)
  4. washthe combined organic phase was washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2cee24aca024f5e91009cbd12cac412
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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