Ammonium Chloride → 1-Methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline

HRID 345855Notes

Reaction equation

HRID 345855 reaction equation
[Br-].[C:2]1([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][N+:9]=2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][Mg]Br.[Cl-].[NH4+]>O1CCCC1.O>[CH3:25][C:8]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 108096381-Phenyl-2-benzyl-3,4-dihydroisoquinolinium bromideHCID 178418573HCID 178418573, compound

Product 1

HCID 106389451-Methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1-phenyl-2-benzyl-3,4-dihydroisoquinolinium bromide (353.1 g) in tetrahydrofuran (3.5 l) was added 2.0M tetrahydrofuran solution of methylmagnesium bromide (700 ml) for 1.5 hours with stirring at room temperature. After additional stirring for 1.5 hours, the mixture was poured into a solution of ammonium chloride (300 g) in water (650 ml) under ice cooling. After separation, the aqueous layer was extracted with ethyl acetate (3.5 l). The combined organic layers were washed with water (1 l), sodium chloride aqueous solution (1 l) and dried over magnesium sulfate (125 g) and evaporated in vacuo. The residue was crystallized from ethanol (500 ml) to give 1-methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline (254.0 g).

Workup

  1. stirringAfter additional stirring for 1.5 hours
  2. customAfter separation
  3. extractionthe aqueous layer was extracted with ethyl acetate (3.5 l)
  4. washThe combined organic layers were washed with water (1 l), sodium chloride aqueous solution (1 l)
  5. dry with materialdried over magnesium sulfate (125 g)
  6. customevaporated in vacuo
  7. customThe residue was crystallized from ethanol (500 ml)

Sources & evidence

ORD record
ord-13d12897274946ce8bacd968eeb6c9fd
Source dataset
uspto-grants-1991_10
Patent number
US05059608

Reaction notes

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