Acetyl chloride → HCID 10506075, compound

HRID 2107653Notes

Reaction equation

HRID 2107653 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:4][C:3]=1[O:34][CH3:35].[C:36](Cl)(=[O:38])[CH3:37]>N1C=CC=CC=1>[C:36]([O:1][C:2]1[C:3]([O:34][CH3:35])=[CH:4][C:5](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:6][C:7]=1[O:8][CH3:9])(=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10412674HCID 10412674, compound

Product 1

HCID 10506075HCID 10506075, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1-[2-{5-(4-hydroxy-3,5-dimethoxyphenyl)-(2E,4E)-2,4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (1 g) and pyridine (10 ml) was added slowly acetyl chloride (0.48 ml) at 5° to 10° C. After 1 hour, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was treated with a mixture of fumaric acid (83 mg) and methanol (8 ml) and concentrated under reduced pressure to give white crystals. The crystals were recrystallized from ethanol to give 1-[2-{5-(4-acetoxy-3,5-dimethoxyphenyl)-(2E,4E)-2,4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine 1/2fumarate (0.25 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was treated with a mixture of fumaric acid (83 mg) and methanol (8 ml)
  9. concentrationconcentrated under reduced pressure
  10. customto give white crystals
  11. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-39369bcfdda347e585c6132a9a9fc994
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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