Formic Acid → HCID 86738423, compound

HRID 1156358Notes

Reaction equation

HRID 1156358 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:5].[CH:29]([OH:31])=[O:30].[CH3:32]C1C=CC=CC=1.[OH2:39]>>[C:16]([OH:24])(=[O:39])/[CH:17]=[CH:22]/[C:29]([OH:31])=[O:30].[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][CH2:7][N:6]3[C:4](=[O:5])[C:3]4[C:2](=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:1]=[CH:32]3)[CH2:11][CH2:12]2)=[O:24])=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 1140TolueneHCID 20278959HCID 20278959, compound

Product 1

HCID 86738423HCID 86738423, compoundYield 54%

Procedure

A mixture of 7 parts of 2-amino-N-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]benzamide, 12 parts of formic acid and 135 parts of methylbenzene is stirred and refluxed for 1 hour. Stirring at reflux is continued for 1 hour using a water-separator. The solvent is evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the (E)-2-butenedioate salt in 2-propanol. The salt is filtered off and dried, yielding 5 parts (54%) of 3-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-4(3H)-quinazolinone (E)-2-butenedioate (1:1); mp. 201.1° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. stirringStirring
  3. temperatureat reflux
  4. customThe solvent is evaporated
  5. customThe oily residue is purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated
  9. filtrationThe salt is filtered off
  10. customdried

Sources & evidence

ORD record
ord-18b8740c39a64ffd91e9a9140942eb46
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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