Allyl iodide → HCID 22406806, compound

HRID 440488Notes

Reaction equation

HRID 440488 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[CH:8]([C:14]1([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:17][CH2:16][CH2:15]1)[NH:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:30](I)[CH:31]=[CH2:32].B(Br)(Br)[Br:35]>CC(C)=O.ClCCl.CO>[BrH:35].[CH2:32]([N:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=2)[CH:8]1[C:14]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:17][CH2:16][CH2:15]1)[CH:31]=[CH2:30]

Participants

8

Reactant 4

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 22406732HCID 22406732, compound

Product 1

HCID 22406806HCID 22406806, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

6-Chloro-7-methoxy-1-(1-phenylcyclobutyl)-1,2,3,4-tetrahydroisoquinoline (1.38 g prepared in a similar manner to that described in Example 59) which was dissolved in acetone (50 ml) and stirred with anhydrous potassium carbonate (1.16 g) and allyl iodide (0.78 g) for one hour. The mixture was filtered and the filtrate concentrated and partitioned between water and ether. The ether layer yielded an oil which was taken up in dichloromethane (30 ml) and cooled to -70° C. A 1M solution of boron tribromide in dichloromethane (11 ml) was added dropwise and the mixture allowed to warm to ambient temperature. After two hours the mixture was cooled to -60° C. and methanol (30 ml) was added cautiously. The solvents were removed and the residue decolourised with charcoal in methanol. Removal of the solvent gave a residue which was recrystallised from a mixture of propan-2-ol and ether to give 2 -allyl-6-chloro-7-hydroxy-1-(1-phenylcyclobutyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 194°-196° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. custompartitioned between water and ether
  4. customThe ether layer yielded an oil which
  5. temperatureto warm to ambient temperature
  6. temperatureAfter two hours the mixture was cooled to -60° C.
  7. customThe solvents were removed
  8. customRemoval of the solvent
  9. customgave a residue which
  10. customwas recrystallised from a mixture of propan-2-ol and ether

Sources & evidence

ORD record
ord-97313d5a644047db89c5146844d10f25
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

Loading…