Acetic Anhydride → HCID 21701629, compound

HRID 1596231Notes

Reaction equation

HRID 1596231 reaction equation
Br.[N:2]1([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].[Na+].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([N:5]1[CH2:6][CH2:7][CH2:8][N:2]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:3][CH2:4]1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 21701666HCID 21701666, compound

Product 1

HCID 21701629HCID 21701629, compound

Procedure

To a solution of N-(1-homopiperazinyl)-4-fluorobenzamide hydrobromide (455 mg) in 1N aqueous solution of sodium hydroxide (3.2 ml) was added acetic anhydride (0.2 ml) at 0° C., and the solution was stirred at ambient temperature for 1.5 hours. The reaction mixture was extracted with a mixture of ethyl acetate and n-butanol. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography eluting with a mixture of methanol and ethyl acetate (1:15) to give oil. The oil was crystallized when treated with ethyl acetate below 0° C. to give N-(4-acetyl-1-homopiperazinyl)-4-fluorobenzamide (137 mg).

Workup

  1. extractionThe reaction mixture was extracted with a mixture of ethyl acetate and n-butanol
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with a mixture of methanol and ethyl acetate (1:15)
  7. customto give oil
  8. customThe oil was crystallized when
  9. additiontreated with ethyl acetate below 0° C.

Sources & evidence

ORD record
ord-7f699110f01b4b45bff5cca4be644656
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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