Allyl bromide → HCID 15590400, compound

HRID 370665Notes

Reaction equation

HRID 370665 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[OH:27])[OH:18])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:34](Br)[CH:35]=[CH2:36].C(OCC)(=O)C>O1CCCC1>[CH2:36]([O:27][C:20]1[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=1[CH:17]([OH:18])[CH2:16][N:13]1[CH2:12][CH2:11][N:10]([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:15][CH2:14]1)[CH:35]=[CH2:34]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 10319868HCID 10319868, compound

Product 1

HCID 15590400HCID 15590400, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

53 mg (2.2 mmol) of sodium hydride was suspended in 5 ml of tetrahydrofuran. To the resultant suspension was added a solution which had been prepared by dissolving 837 mg (2 mmol) of 2-(4-diphenylmethylpiperazinyl)-1-(2-hydroxy-4-methoxyphenyl)ethanol in 5 ml of tetrahydrofuran under ice-cooled conditions. Thereafter, 2 ml of a tetrahydrofuran solution of 266 mg (2.2 mmol) of allylbromide was added and heated with refluxing for 4 hours. After being cooled to room temperature, the resultant mixture was added with 50 ml of ethyl acetate. The mixture was then washed successively with water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was removed, and the residue was subjected to thin-layer chromatography to give 419 mg of 1-(2-allyloxy-4-methoxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanol as a colorless oily substance (yield: 46%).

Workup

  1. customhad been prepared
  2. temperaturecooled conditions
  3. temperatureheated
  4. temperaturewith refluxing for 4 hours
  5. washThe mixture was then washed successively with water and saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-37e5aa45593247efa759165f6e926224
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Reaction notes

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