Benzoyl chloride → HCID 19011942, compound

HRID 1729301Notes

Reaction equation

HRID 1729301 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C([Li])CCC.CCCCCC.[C:33]([Cl:41])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[ClH:41].[C:33]([C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8058HexaneHCID 21993766tert-Butyl 4-(2-phenylethyl)piperazine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 19011942HCID 19011942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 g of 1-(t-butyloxycarbonyl)-4-(2-phenylethyl)piperazine was dissolved in 8 ml of tetrahydrofuran, and 2.8 ml of butyllithium (1.6N, a hexane solution) was added dropwise to the solution at -30° C. followed by stirring for 30 minutes. Next, 0.88 ml of benzoyl chloride was added thereto, and the solution was stirred for 3 hours, poured into ice water, and then extracted with 50 ml of chloroform. The resultant chloroform layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated, and the residue was separated through a silica gel column chromatograph (hexane/ethyl acetate=1/1). The resultant oil dissolved in 10 ml of ether, and 4.8 ml of a 4N hydrochloric acid/dioxane solution was added thereto, followed by stirring at room temperature for 30 minutes. The precipitated crystals were collected by filtration, whereby 0.36 g of 1-2-[2-benzoylphenyl]ethyl)piperazine.hydrochloride was obtained.

Workup

  1. stirringthe solution was stirred for 3 hours
  2. extractionextracted with 50 ml of chloroform
  3. washThe resultant chloroform layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe residue was separated through a silica gel column chromatograph (hexane/ethyl acetate=1/1)
  7. dissolutionThe resultant oil dissolved in 10 ml of ether
  8. addition4.8 ml of a 4N hydrochloric acid/dioxane solution was added
  9. stirringby stirring at room temperature for 30 minutes
  10. filtrationThe precipitated crystals were collected by filtration, whereby 0.36 g of 1-2-[2-benzoylphenyl]ethyl)piperazine.hydrochloride
  11. customwas obtained

Sources & evidence

ORD record
ord-4bcadc8e0ad84a6ca1b431ac558c93c1
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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