Acetic Anhydride → HCID 14304633, compound

HRID 414060Notes

Reaction equation

HRID 414060 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:16][CH2:15]3)[C:8](=[O:27])[NH:7][C:6]=2[CH:28]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:16][CH2:15]3)[C:8](=[O:27])[NH:7][C:6]=2[CH:28]=1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14304632HCID 14304632, compound

Product 1

HCID 14304633HCID 14304633, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-amino-2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-2H-1,4-benzoxazin-3(4H)-one (500 mg) in pyridine (5 ml) was added acetic anhydride (0.18 ml) while stirring. The mixture was stirred at room temperature for further 4 hours, which was then poured into ice-water. Precipitated crystals were collected by filtration, followed by recrystallization from dichloromethane-ethyl acetate to give 397 mg (71.5%) of 6-acetamido-2-{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}-2H-1,4-benzoxazin-3(4H)-one, m.p. 111°-112° C.

Workup

  1. stirringThe mixture was stirred at room temperature for further 4 hours
  2. customPrecipitated crystals
  3. filtrationwere collected by filtration
  4. customfollowed by recrystallization from dichloromethane-ethyl acetate

Sources & evidence

ORD record
ord-e43718e63d88458b9fe39fea26d7b292
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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