Bromomethylstyrene → HCID 70622914, compound

HRID 1703790Notes

Reaction equation

HRID 1703790 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:27](Br)[CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)C>[ClH:1].[ClH:1].[CH2:27]([N:19]1[CH2:18][CH2:17][N:16]([CH:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:13][CH:12]=2)[CH3:15])[CH2:21][CH2:20]1)[CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 98116BromomethylstyreneHCID 516892Sodium BicarbonateHCID 22760364HCID 22760364, compound

Product 1

HCID 70622914HCID 70622914, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 8g of 1[1-(4'-chloro[1,1']biphenyl-4-yl)ethyl]piperazine, 2.7g of sodium bicarbonate in 75 ml of absolute ethanol, add in a dropwise fashion 5.25g of cinnamyl bromide. Reflux the reaction mixture for 6 hours, concentrate in vacuo, and treat with 50 ml of 10% hydrochloric acid solution. Filter the dihydrochloride and recrystallize from 80% ethanol, m.p. 273°-275°. The free base has a melting point of 108°-109° after recrystallization from acetonitrile.

Workup

  1. temperatureReflux the reaction mixture for 6 hours
  2. concentrationconcentrate in vacuo
  3. additiontreat with 50 ml of 10% hydrochloric acid solution
  4. filtrationFilter the dihydrochloride
  5. customrecrystallize from 80% ethanol, m.p. 273°-275°
  6. customafter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-eb58a244c9494a41be050fdf25d9dd1d
Source dataset
uspto-grants-1978_11
Patent number
US04125612

Reaction notes

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