Acetic Acid → HCID 18542808, compound

HRID 1268190Notes

Reaction equation

HRID 1268190 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].[C:33](O)(=O)[CH3:34].[C:37]([BH3-])#N.[Na+].O>CC(C)=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])[CH:33]([CH3:34])[CH3:37])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 18542676HCID 18542676, compound

Product 1

HCID 18542808HCID 18542808, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzonitrile (1500 mg) in acetone (20 ml) were added acetic acid (0.20 ml) and sodium cyanoborohydride (214 mg) in an ice bath. The mixture was stirred at room temperature overnight and then heated under reflux for 8 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1 as an eluant to give the desired compound (583 mg, yield 35%) as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialThe organic layer was dried 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-96bf2e36b7db44b2824a2b75e3b6b468
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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