Toluene → HCID 12852070, compound

HRID 1248246Notes

Reaction equation

HRID 1248246 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:5].C(OC(=O)C)(=[O:29])C.C[C:35]1[CH:40]=CC=CC=1>>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:1]=[C:40]3[CH3:35])[CH2:10][CH2:11]2)=[O:29])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 20278972HCID 20278972, compound

Product 1

HCID 12852070HCID 12852070, compoundYield 69%

Procedure

A mixture of 6 parts of 2-amino-N-[2-[4-(4-fluorobenzyl)-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-a443e8299cae40e18de1e0158759117c
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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