Allyl bromide → HCID 13109061, compound

HRID 1462974Notes

Reaction equation

HRID 1462974 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)=[CH:4][C:3]=1[O:23][CH3:24].[CH2:25](Br)[CH:26]=[CH2:27].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:27]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([OH:1])=[C:3]([O:23][CH3:24])[CH:4]=2)[CH:9]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 11186519(-)-7-Hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 13109061HCID 13109061, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

27.7 g. (84 mmol) (-)-7-Hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in 430 ml. ethanol are mixed with 9.18 g. (75.9 mmol) allyl bromide and 17.6 g. (209 mmol) sodium bicarbonate. The reaction mixture is heated for 3 hours at 80° C., while stirring. After cooling and evaporating in a vacuum, the residue is partitioned between water and methylene chloride. The usual working up and chromatographic purification (silica gel; chloroform) gives 22.0 g. of a pale yellow foam. By crystallisation from isopropanol-diethyl ether, there is obtained (+)-2-allyl-7-hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in the form of colourless crystals; m.p. 108°-112° C.

Workup

  1. temperatureAfter cooling
  2. customevaporating in a vacuum
  3. customthe residue is partitioned between water and methylene chloride
  4. customchromatographic purification (silica gel; chloroform)
  5. customgives 22.0 g
  6. customBy crystallisation from isopropanol-diethyl ether

Sources & evidence

ORD record
ord-7c3d04568fec470d9bada7e0b88740cf
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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