Water → HCID 54531771, compound

HRID 1395242Notes

Reaction equation

HRID 1395242 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH:28]=[CH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:23][CH2:22]1.O>C1(C)C(C)=CC=CC=1>[CH3:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:15][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH:28]=[CH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:23][CH2:22]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 95377Benzenemethanol, 4-methyl-.alpha.-phenyl-HCID 54353609HCID 54353609, compound

Product 1

HCID 54531771HCID 54531771, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

2 g of 60% sodium hydride in paraffin oil were added to a solution of 10 g (0.05 mol) of 4-methylbenzhydrol in 100 ml of anhydrous xylene. The reaction mixture was refluxed for half an hour and then 12.7 g (0.05 mol) of 1-(2-chloroethyl)-4-(3-phenyl-2-propenyl)piperazine (German pat.appl.2.431.178) in 50 ml of xylene were added dropwise. The reaction mixture was refluxed for another three hours and then cooled and poured into water. The organic layer was separated off, washed with water and concentrated. The residue was purified by column chromatography (Silicagel) with chloroform/ethylacetate/methanol/ammonia (25:25:1:0.5) as the eluent which yielded 1-[2-[(4-Methylphenyl)phenylmethoxy]ethyl]-4-(3-phenyl-2-propenyl)piperazine.

Workup

  1. temperatureThe reaction mixture was refluxed for half an hour
  2. temperatureThe reaction mixture was refluxed for another three hours
  3. temperaturecooled
  4. customThe organic layer was separated off
  5. washwashed with water
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (Silicagel) with chloroform/ethylacetate/methanol/ammonia (25:25:1:0.5) as the eluent which

Sources & evidence

ORD record
ord-fb571a6e411741f2b85224b86a1b4756
Source dataset
uspto-grants-1980_05
Patent number
US04202896

Reaction notes

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