Sodium Hydroxide → HCID 135502993, compound

HRID 1156357Notes

Reaction equation

HRID 1156357 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 2 N 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-c0b9be75629e44e19d35e15b5b7dcc0f
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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