Dimethyl Sulfoxide → HCID 21537802, compound

HRID 1076787Notes

Reaction equation

HRID 1076787 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1([CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:22][Cl:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Ca+2].CS(C)=O>O.CCOCC.C(O)(CC)C>[ClH:23].[ClH:23].[C:14]1([CH:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:21][CH2:22][N:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10112Calcium CarbonateHCID 759941-BenzylpiperazineHCID 1901351,1'-(3-Chloropropane-1,1-diyl)dibenzene

Product 1

HCID 21537802HCID 21537802, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

N-benzylpiperazine in the amount of 1.76 g (0.01 mole), 2.3 g (0.01 mole) of 3,3-diphenylpropyl chloride, 1.5 g (0.015 mole) of calcium carbonate, and 2 ml of dimethyl sulfoxide were mixed with 20 ml of secondary butanol, and the resulting solution was heated at the refluxing temperature for 2.5 hours. The reaction liquid was filtered after being left to cool, and the filtrate was concentrated under reduced pressure to produce an oily residue, which was shaken with ether and water, and the ether layer dried. Then, dry hydrogen chloride gas was passed through the ether solution while cooling the solution to precipitate 1 -(3,3-diphenylpropyl)-4-benzylpiperazine dihydrochloride, whose crystals were recrystallized from methanol to obtaine 3.6 g (81.2% yield) of pure crystals with a melting point of 187° -188°C.

Workup

  1. temperaturethe resulting solution was heated at the refluxing temperature for 2.5 hours
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. waitafter being left
  5. temperatureto cool
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto produce an oily residue, which
  8. dry with materialthe ether layer dried
  9. temperaturewhile cooling the solution
  10. customto precipitate 1 -(3,3-diphenylpropyl)-4-benzylpiperazine dihydrochloride, whose crystals
  11. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-78b92797a10140acb6866b7b2fe4b2f3
Source dataset
uspto-grants-1976_05
Patent number
US03957790

Reaction notes

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