Acetic Anhydride → HCID 12852070, compound

HRID 1156360Notes

Reaction equation

HRID 1156360 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:5].[C:28](OC(=O)C)(=O)[CH3:29]>CC1C=CC=CC=1>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:1]=[C:28]3[CH3:29])[CH2:14][CH2:13]2)=[O:23])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 30186512-Amino-N-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}benzene-1-carboximidic acid

Product 1

HCID 12852070HCID 12852070, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6 parts of 2-amino-N-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]benzamide, 10 parts of acetic acid anhydride and 108 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is evaporated and water is added to the oily residue. The whole is alkalized with a dilute sodium hydroxide solution and extracted with trichloromethane. The extract is dried, filtered and evaporated. The oily residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and recrystallized from 2-propanol, yielding 4.4 parts (69%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4(3H)-quinazolinone; mp. 164.9° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the oily residue
  4. extractionextracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe oily residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-2948e088ab744011aaca82c7c0f5233c
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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