Acetic Anhydride → HCID 70072529, compound

HRID 344558Notes

Reaction equation

HRID 344558 reaction equation
[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)=[O:22])[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:33][CH3:34])[CH:3]=1.C(N(CC)CC)C.[C:42]([O:45]C(=O)C)(=[O:44])[CH3:43]>ClCCl>[C:42]([OH:45])(=[O:44])[CH3:43].[NH2:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:42](=[O:44])[CH3:43])=[CH:27][CH:28]=3)=[O:22])[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:33][CH3:34])[CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 53646252HCID 53646252, compound

Product 1

HCID 70072529HCID 70072529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-amino-5-chloro-2-methoxy-N-((1-(6-(4-hydroxyphenyl)-6-oxohexyl)piperidin-4-yl)methyl)benzamide (10.0 g) in dichloromethane (60 ml) were added triethylamine (12.5 ml) and acetic anhydride (2.5 ml), and the resulting mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the obtained crystals were recrystallized from a mixed solvent of ethanolethyl acetate to give 8.50 g of 4-amino-5-chloro-2-methoxy-N-((1-(6-(4-acetoxyphenyl)-6-oxohexyl)piperidin-4-yl)methyl)benzamide acetate, m.p. 140°-141° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained crystals were recrystallized from a mixed solvent of ethanolethyl acetate

Sources & evidence

ORD record
ord-df37162552e848d3b598ba95b42da9be
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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