Sodium Hydroxide → HCID 135502993, compound

HRID 1248243Notes

Reaction equation

HRID 1248243 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=O)[CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)=[O:3].[OH-].[Na+]>C(O)C>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][C:11]3[NH:1][C:2](=[O:3])[C:4]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:10]=3)[CH2:16][CH2:17]2)=[O:29])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20278953HCID 20278953, compound

Product 1

HCID 135502993HCID 135502993, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 parts of N-[2-(aminocarbonyl)phenyl]-4-(4-fluorobenzoyl)-1-piperidinebutanamide, 60 parts of sodium hydroxide solution 2N and 80 parts of ethanol is stirred and refluxed for 1.50 hours. The reaction mixture is evaporated and water is added to the residue. The oily product is dissolved in trichloromethane. The solution is dried, filtered and evaporated. The residue is crystallized twice from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 1 part (10.5%) of 2-[3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl]-4(3H)-quinazolinone; mp. 184° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. dissolutionThe oily product is dissolved in trichloromethane
  5. customThe solution is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized twice from 4-methyl-2-pentanone
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-80576492ad3b42fd8bb19283c5c473a7
Source dataset
uspto-grants-1985_06
Patent number
US04522945

Reaction notes

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