Water → HCID 19844666, compound

HRID 2351886Notes

Reaction equation

HRID 2351886 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH2:10][CH3:11].[C:27](=[O:30])([O-:29])[O-].[K+].[K+].[CH2:33](Br)[CH:34]=[CH2:35].[OH2:37]>C1C=CC=CC=1>[C:9]([OH:37])(=[O:12])/[CH:21]=[CH:26]/[C:27]([OH:29])=[O:30].[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:35][CH:34]=[CH2:33])[CH2:17][CH2:16]1)[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 19844683HCID 19844683, compound

Product 1

HCID 19844666HCID 19844666, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture containing 10.6 g of 1-[2-[1-(2,5-dimethylphenyl)-1-phenylpropoxy]ethyl]piperazine and 4.6 g of anhydrous, powdered potassium carbonate in 90 ml of anhydrous benzene, 3.6 g of allyl bromide dissolved in 10 ml of benzene are dropped while mild refluxing, then the reaction mixture is boiled for one additional hour. After cooling down, water is added to the mixture, the organic phase is separated, washed with water until neutral, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The anhydrous ethanolic solution of the evaporation residue is treated with an ethanolic fumaric acid solution. The solid precipitate is recrystallized from methanol to give the aimed dihydrogen fumarate, m.p. 202°-204° C.

Workup

  1. additionare dropped while mild refluxing
  2. temperatureAfter cooling down
  3. customthe organic phase is separated
  4. washwashed with water until neutral,
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. additionThe anhydrous ethanolic solution of the evaporation residue is treated with an ethanolic fumaric acid solution
  8. customThe solid precipitate is recrystallized from methanol

Sources & evidence

ORD record
ord-aa3b11f26b6d4db58de04161297c096c
Source dataset
uspto-grants-1989_10
Patent number
US04874765

Reaction notes

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