1-Phenylpiperazine → HCID 15623643, compound

HRID 1462896Notes

Reaction equation

HRID 1462896 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:12]([CH3:18])[C:13](=O)[CH2:14][CH2:15]Cl.[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC=CC=1>[CH3:18][N:12]1[C:3]2[CH:4]=[CH:5][C:6]3[C:11]([C:2]=2[N:1]=[C:13]1[CH2:14][CH2:15][N:28]1[CH2:29][CH2:30][N:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:26][CH2:27]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 70961-Phenylpiperazine2×HCID 20452287HCID 20452287, compound

Product 1

HCID 15623643HCID 15623643, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of 5.25 g (0.02 mole) of N-(1-amino-2-naphthyl)-3-chloro-N-methyl-propanamide in 150 cc of anhydrous benzene is gradually added to a solution of 9.73 g (0.06 mole) of 1-phenylpiperazine in 25 cc of anhydrous benzene under argon atmosphere over a period of time of twenty minutes. The reaction mixture is then refluxed for 21 hours. Further, 11.73 g (0.0724 mole) of 1-phenylpiperazine is added and reflux is continued for an additional 24 hours. After cooling to room temperature, the mixture is diluted with 350 cc of benzene, poured into a separatory funnel and washed with 100 cc of water containing 7.8 cc of acetic acid. The benzene phase is extracted four times with 40 cc portions of 8% HCl. The pH of the aqueous acid phase is brought to 9 by addition of concentrated NH4OH and this aqueous solution is extracted with methylene chloride. The organic extracts are combined, dried over Na2SO4 , filtered and evaporated to dryness yielding 4.03 g of raw compound which is recrystallized from 25 cc of ethanol. M.p. 153°-155° C.

Workup

  1. temperatureThe reaction mixture is then refluxed for 21 hours
  2. temperaturereflux
  3. additionpoured into a separatory funnel
  4. washwashed with 100 cc of water containing 7.8 cc of acetic acid
  5. extractionThe benzene phase is extracted four times with 40 cc portions of 8% HCl
  6. additionThe pH of the aqueous acid phase is brought to 9 by addition of concentrated NH4OH
  7. extractionthis aqueous solution is extracted with methylene chloride
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-4b2c9aa5dd8c49f0b08639044be2644f
Source dataset
uspto-grants-1984_07
Patent number
US04461894

Reaction notes

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