1-Phenylpiperazine → HCID 18993040, compound

HRID 375542Notes

Reaction equation

HRID 375542 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[C:6]1([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OCC)C>[CH2:2]([N:15]1[CH2:16][CH2:17][N:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:13][CH2:14]1)[CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 21241Homoallyl bromide

Product 1

HCID 18993040HCID 18993040, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-bromobut-1-ene (8.68 g) and 1-phenylpiperazine (35.7 g) is heated to reflux in diethyl ether (100 mL) for 2 hours. The mixture is filtered and the filtrate is extracted with 2N hydrochloric acid (150 mL). The extracts are washed with diethyl ether (150 mL) and basified with 25% sodium hydroxide. The aqueous layer is extracted with diethyl ether (3×100 mL), the extracts dried over MgSO4, filtered and evaporated to leave a brown oil. This oil is purified by MPLC on silica gel eluting with 5% methanol in dichloromethane to give 10.4 g of the title compound as a yellow oil.

Workup

  1. temperatureis heated
  2. filtrationThe mixture is filtered
  3. extractionthe filtrate is extracted with 2N hydrochloric acid (150 mL)
  4. washThe extracts are washed with diethyl ether (150 mL)
  5. extractionThe aqueous layer is extracted with diethyl ether (3×100 mL)
  6. dry with materialthe extracts dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto leave a brown oil
  10. customThis oil is purified by MPLC on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-1ad1a11b83a649e0a396f67bde226d4c
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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