Benzyl Bromide → HCID 14625296, compound

HRID 1089308Notes

Reaction equation

HRID 1089308 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([OH:14])[CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[K+]>C(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:14][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 2752175HCID 2752175, compound

Product 1

HCID 14625296HCID 14625296, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-Acetyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline quarter-hydrate (14.0 g) was dissolved in methylene chloride (200 ml). Benzyl bromide (22.6 ml) was then added, followed by the addition of a solution of potassium hydroxide (4.62 g) in water (200 ml) and then tetra-n-butylammonium bromide (2.04 g). The resulting mixture was stirred vigorously overnight (16 hours). The organic layer was then separated, washed (H2O), dried (MgSO4) and evaporated. Medium pressure chromatography of the residue on silica (Merck "Art.9385") eluting with methylene chloride containing gradually increasing amounts of methanol (0-10%) gave, after collection and evaporation of appropriate fractions, the title compound as a semi-solid which was recrystallised from ethyl acetate to give the pure title compound, 16.84 g, m.p. 125°-6°.

Workup

  1. customThe organic layer was then separated
  2. washwashed (H2O)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. washMedium pressure chromatography of the residue on silica (Merck "Art.9385") eluting with methylene chloride containing gradually increasing amounts of methanol (0-10%)
  6. customgave
  7. customafter collection and evaporation of appropriate fractions
  8. customthe title compound as a semi-solid which was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b99c534fd2ba4ce2b672279c8aebd96b
Source dataset
uspto-grants-1990_10
Patent number
US04965360

Reaction notes

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