Glutaric anhydride → 5-[4-(Methylphenylcarbamoylmethyl)piperazin-1-yl]-5-oxopentanoic acid

HRID 1374587Notes

Reaction equation

HRID 1374587 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[N:9]1([CH2:15][C:16]([N:18](C)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.O1CCOC[CH2:27]1>>[CH3:27][CH:15]([C:16](=[O:17])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:9]1[CH2:14][CH2:13][N:12]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 7940Glutaric anhydrideHCID 312751,4-DioxaneHCID 2737187N-methyl-N-phenyl-2-(piperazin-1-yl)acetamide

Product 1

HCID 695033575-[4-(Methylphenylcarbamoylmethyl)piperazin-1-yl]-5-oxopentanoic acid

Conditions

Temperature
25 °C

Procedure

1.517 g of glutaric anhydride and then 1.715 g of N-[2-(piperazin-1-yl)acetyl]-N-methylaniline are added to 15 cm3 of dioxane. After stirring for 19 hours at 25° C., the white precipitate formed is filtered on No. 4 sintered glass, rinsed with dioxane and then with diethyl ether and then dried at 20° C. (90 Pa) to give 2 g of 5-[4-(methylphenylcarbamoylmethyl)piperazin-1-yl]-5-oxopentanoic acid in the form of a white solid which is used as it is.

Workup

  1. customthe white precipitate formed
  2. filtrationis filtered on No
  3. wash4 sintered glass, rinsed with dioxane
  4. dry with materialwith diethyl ether and then dried at 20° C. (90 Pa)

Sources & evidence

ORD record
ord-39a99c2913fe4965814b43325565eac7
Source dataset
uspto-grants-2007_01
Patent number
US07166594B2

Reaction notes

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