Hydrochloric Acid → HCID 12852071, compound

HRID 1248247Notes

Reaction equation

HRID 1248247 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH2:10])=[O:9].Cl.C(O[CH:15](OCC)[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:25])[CH2:20][CH2:19]1)C>C(O)C>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH:15]3[NH:10][C:8](=[O:9])[C:3]4[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=4)[NH:1]3)[CH2:19][CH2:20]2)=[O:25])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6942AnthranilamideHCID 20278954HCID 20278954, compound

Product 1

HCID 12852071HCID 12852071, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9 parts of 2-aminobenzenecarboxamide, 12 parts of concentrated hydrochloric acid and 120 parts of absolute ethanol is stirred and refluxed for 2 hours. Then there are added 3.6 parts of [1-(3,3-diethoxypropyl)-4-piperidinyl](4-fluorophenyl)methanone and stirring at reflux is continued overnight. The reaction mixture is evaporated and the residue is stirred with water. The whole is alkalized with ammonia and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized twice from 4-methyl-2-pentanone, yielding 1.9 parts (19%) of 2-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3-dihydro-4(1H)-quinazolinone; mp. 153.4° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. stirringstirring
  3. temperatureat reflux
  4. customThe reaction mixture is evaporated
  5. stirringthe residue is stirred with water
  6. extractionthe product is extracted with trichloromethane
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated
  14. customThe residue is crystallized twice from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-0b4d392494c2448caa1efbb9f78a6a35
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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