Pirenperone → 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Z)-2-butenedioate

HRID 66687Notes

Reaction equation

HRID 66687 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[C:21](=[O:22])[N:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]4=[N:18][C:17]=3[CH3:27])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>CC(O)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]3[C:21](=[O:22])[N:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]4=[N:18][C:17]=3[CH3:27])[CH2:12][CH2:13]2)=[O:7])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 4847PirenperoneHCID 444266Maleic Acid

Product 1

HCID 867385183-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Z)-2-butenedioateYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a stirred solution of 2 parts of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one in 32 parts of 2-propanol is added a solution of 0.59 parts of (Z)-2-butenedioic acid in 16 parts of 2-propanol. The product is allowed to crystallize. It is filtered off and dried, yielding 2.1 parts (82%) of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (Z)-2-butenedioate (1:1); mp. 180.2° C.

Workup

  1. customto crystallize
  2. filtrationIt is filtered off
  3. customdried

Sources & evidence

ORD record
ord-5f37c8aec7934ea29fd613f1641ba001
Source dataset
uspto-grants-1982_08
Patent number
US04342870

Reaction notes

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