Acetic Acid → HCID 18542812, compound

HRID 1268188Notes

Reaction equation

HRID 1268188 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=O.[C:35](O)(=O)C.C([BH3-])#N.[Na+]>ClCCl.CO>[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])[CH3:35])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18542676HCID 18542676, compound

Product 1

HCID 18542812HCID 18542812, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzonitrile (1000 mg) and paraformaldehyde (138 mg) in dichloromethane (20 ml) were added acetic acid (0.26 ml) and sodium cyanoborohydride (144 mg) in an ice bath. The mixture was stirred at room temperature overnight and then methanol (20 ml) was added. The resulting mixture was stirred at 30° C. for 5 hours. The reaction mixture was partitioned between water and ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=3/2 as an eluant to give the desired compound (761 mg, yield 74%) as a yellow oil.

Workup

  1. stirringThe resulting mixture was stirred at 30° C. for 5 hours
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-eed02e7e5fdf4d29a4c86abcc51a1b55
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

Loading…