Phenethyl bromide → HCID 20076658, compound

HRID 1654662Notes

Reaction equation

HRID 1654662 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][N:2]=1.[Br:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[Br-:11].[CH2:12]([N+:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:1]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 1190105,6,7,8-Tetrahydroisoquinoline

Product 1

HCID 20076658HCID 20076658, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.05 g of 5,6,7,8-tetrahydroisoquinoline, 4.30 g of 2-bromoethylbenzene, and 5 mL of dimethylformamide was stirred in a 75°-80° oil bath for 4 hours. The solvent was removed under vacuum, the residue was dissolved in 4 mL of acetonitrile and 8 mL of 1-chlorobutane were added. The precipitate was collected after 1 hour to give 3.28 g of 2-phenethyl-5,6,7,8-tetrahydroisoquinolinium bromide.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in 4 mL of acetonitrile
  3. addition8 mL of 1-chlorobutane were added
  4. customThe precipitate was collected after 1 hour

Sources & evidence

ORD record
ord-5b93cdcbb3984f0cb8ebb767bb76066d
Source dataset
uspto-grants-1995_04
Patent number
US05409929

Reaction notes

Loading…