Benzene → HCID 19370330, compound

HRID 129734Notes

Reaction equation

HRID 129734 reaction equation
[CH3:1][C:2]([OH:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.[NH2-].[Na+].C1C=CC=CC=1>O>[CH2:28]([O:27][C:25]([N:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][O:15][C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:1])[CH2:24][CH2:23]1)=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 241BenzeneHCID 24533Sodium amideHCID 69031Benzenemethanol, .alpha.-methyl-.alpha.-phenyl-HCID 201594Ethyl 4-(2-chloroethyl)piperazine-1-carboxylate

Product 1

HCID 19370330HCID 19370330, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.8 g (9.1 mmole) of α-methylbenzhydrol, 2.0 g (9.1 mmole) of 1-(2-chloroethyl)-4-(ethoxycarbonyl)piperazine, 0.36 g (9.2 mmole) of sodium amide and 20 ml of benzene was heated under reflux overnight. At the end of this time, water was poured onto the reation mixture, and the mixture was extracted with ethyl acetate. The solvent was then removed from the mixture by distillation under reduced pressure, and the residue was subjected to column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to obtain 2.5 g (yield 75%) of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe solvent was then removed from the mixture by distillation under reduced pressure
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-4ae16e94a4e6460f9a388a43b50f8ca0
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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