Hexane → 1-(4-Bromophenyl)-6-methoxy-3,4-dihydroisoquinoline hydrochloride

HRID 397052Notes

Reaction equation

HRID 397052 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:22].CCCCCC>C(Cl)(Cl)Cl>[ClH:22].[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24819Phosphorus pentachlorideHCID 110241034-bromo-N-[2-(3-methoxyphenyl)ethyl]benzamide

Product 1

HCID 181724611-(4-Bromophenyl)-6-methoxy-3,4-dihydroisoquinoline hydrochlorideYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-bromo-N-[2-(3-methoxyphenyl)ethyl]benzamide (5.00 g, 15.0 mmol) in CHCl3 (30 ml) was added phosphorous pentachloride (5.30 g, 25.0 mmol) and the mixture stirred for 18 hr at rt under N2. Hexane was added to the mixture and the liquid was then decanted off. EtOH (15 ml) was added to the residue and the mixture was triturated with diethyl ether to give 3.65 g (69% yield) of off-white solid.

Workup

  1. customthe liquid was then decanted off
  2. additionEtOH (15 ml) was added to the residue
  3. customthe mixture was triturated with diethyl ether

Sources & evidence

ORD record
ord-1ac3f707267e41fa8e00cbe33e0b9d5b
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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