Benzene → 2-[2-[4-(Diphenylmethyl)-1-piperazinyl]ethoxy]-acetamide

HRID 1248575Notes

Reaction equation

HRID 1248575 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:21][CH2:22][O:23][CH2:24][C:25]([NH2:27])=[O:26].C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][O:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 70048BenzhydrylpiperazineHCID 110189312-(2-Chloroethoxy)acetamide

Product 1

HCID 30688392-[2-[4-(Diphenylmethyl)-1-piperazinyl]ethoxy]-acetamideYield 73%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 37.8 g (0.15 mole) of 1-(diphenylmethyl)-piperazine, 27.5 g (0.2 mole) of 2-(2-chloroethoxy)-acetamide and 26.5 g of anhydrous sodium carbonate in 120 ml of xylene is heated for 4 hours to 90° to 120° C. Thereafter, 120 ml of benzene are added to the reaction mixture, the precipitate formed is filtered off and the organic phase is extracted with dilute hydrochloric acid (30 ml of concentrated hydrochloric acid and 100 ml of water). 40 ml of a concentrated aqueous solution of sodium hydroxide are added, followed by extraction with benzene. The benzene solution is washed with water, dried over anhydrous sodium carbonate and the benzene is evaporated off to dryness. The evaporation residue is triturated with diethyl ether and left to crystallize. 2-[2-[4-(Diphenylmethyl)-1-piperazinyl]ethoxy]-acetamide is obtained in a yield of 73% of theory; M.P. 119°-120° C.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. extractionthe organic phase is extracted with dilute hydrochloric acid (30 ml of concentrated hydrochloric acid and 100 ml of water)
  4. addition40 ml of a concentrated aqueous solution of sodium hydroxide are added
  5. extractionfollowed by extraction with benzene
  6. washThe benzene solution is washed with water
  7. dry with materialdried over anhydrous sodium carbonate
  8. customthe benzene is evaporated off to dryness
  9. customThe evaporation residue is triturated with diethyl ether
  10. waitleft
  11. customto crystallize

Sources & evidence

ORD record
ord-92ae43157e9a4f35b58fd2afe789a115
Source dataset
uspto-grants-1985_06
Patent number
US04525358

Reaction notes

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