Allyl bromide → N-allyl-8,9-dimethoxy-1,2,3,11b-tetrahydrochromeno [4,3,2-de]isoquinoline

HRID 895402Notes

Reaction equation

HRID 895402 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[C:11]4[CH:12]([CH2:13][NH:14][CH2:15][C:16]=4[CH:17]=[CH:18][CH:19]=3)[C:7]=2[CH:6]=[CH:5][C:4]=1[O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CC(C)=O>[CH2:30]([N:14]1[CH2:13][CH:12]2[C:7]3[CH:6]=[CH:5][C:4]([O:20][CH3:21])=[C:3]([O:2][CH3:1])[C:8]=3[O:9][C:10]3[C:11]2=[C:16]([CH:17]=[CH:18][CH:19]=3)[CH2:15]1)[CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 129719228,9-Dimethoxy-1,2,3,11b-tetrahydrochromeno[4,3,2-de]isoquinoline

Product 1

HCID 12971923N-allyl-8,9-dimethoxy-1,2,3,11b-tetrahydrochromeno [4,3,2-de]isoquinolineYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Tetrahydroisoquinoline 7a (1.273 g; 4.5 mmol) was dissolved in 150 ml of acetone. Potassium carbonate (0.613 g; 4.5 mmol) and 0.4 ml (4.6 mmol) of allyl bromide were added. The reaction was stirred at room temperature for four hours. The solid was then removed by filtration and washed on the filter several times with ether. The filtrate was concentrated and purified by flash chromatography (silica gel, 50% ethyl acetate:hexane) to give 1.033 g (71%) of a yellow oil that was used without further purification: 1H NMR: (300 MHz, CDCl3): 7.15 (t, 1H, J=9 Hz); 7.04 (d, 1H, J=9 Hz); 6.83 (m, 2H); 6.65 (d, 1H, J=6 Hz); 5.98 (m, 1H); 5.27 (m, 2H); 4.10 (m, 3H); 3.95 (s, 3H); 3.86 (s, 3H); 3.46 (d, 1H, J=15 Hz); 3.30 (d, 2H, J=6 Hz); 2.56 (t, 1H, J=12 Hz).

Workup

  1. customThe solid was then removed by filtration
  2. washwashed on the filter several times with ether
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (silica gel, 50% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-022d6284470b4489afe990728096454c
Source dataset
uspto-grants-2005_07
Patent number
US06916823B2

Reaction notes

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