Acetic Acid → HCID 18542608, compound

HRID 1268189Notes

Reaction equation

HRID 1268189 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:33](=O)[CH3:34].C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCl.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])[CH2:33][CH3:34])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18542676HCID 18542676, compound

Product 1

HCID 18542608HCID 18542608, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzonitrile (1000 mg) and acetaldehyde (0.52 ml) in a mixture of dichloromethane (10 ml) and methanol (20 ml) were added acetic acid (0.26 ml) and sodium cyanoborohydride (144 mg) in an ice bath. The mixture was stirred at the same temperature for 2 hours and then at room temperature overnight. To the reaction mixture was added water, and the mixture was then extracted with ethyl acetate. The extractant was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1→2/1 as an eluant to give the desired compound (661 mg, yield 62%) as a yellow oil.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture was then extracted with ethyl acetate
  4. washThe extractant was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ed41432402e7430b9e476f88dd1a603b
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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