1-Phenylpiperazine → 5-Hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one

HRID 1942405Notes

Reaction equation

HRID 1942405 reaction equation
CCN(CC)CC.[Al+3].[Cl-].[Cl-].[Cl-].[C:12]1([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:24]1(=[O:30])[O:29][CH2:28][CH2:27][CH2:26][CH2:25]1>ClC(Cl)C.ClCCCl>[OH:30][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([N:21]1[CH2:22][CH2:23][N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][CH2:20]1)=[O:29]

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 10953Delta-ValerolactoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 669376015-Hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 5.4 mL (37.5 mmol) Et3N in 10 ml, 2-dichloroethane was added drop by drop under ice cooling to a suspension of 3.70 g (27.5 mmol) AlCl3 in 20mL dichloroethane. At room temperature a solution of 4.21 ml (27.5 mmol) 1-phenylpiperazine and 2.32 mL (25 mmol) delta-valerolactone in 15 mL 1,2-dichloroethane was added to the mixture. After one hour of stirring at room temperature the mixture was quenched with ice water and stirred for another 30 minutes. The suspension was filtered by Celite. After adding of dichloromethane, separating of the organic layer, washing it with water, drying it with Na2SO4 and evaporating of the solvent, followed.

Workup

  1. customwas quenched with ice water
  2. stirringstirred for another 30 minutes
  3. filtrationThe suspension was filtered by Celite
  4. additionAfter adding of dichloromethane
  5. customseparating of the organic layer
  6. washwashing it with water
  7. dry with materialdrying it with Na2SO4
  8. customevaporating of the solvent

Sources & evidence

ORD record
ord-3623fe177a8644d8a739693668af63b0
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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