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

HRID 345853Notes

Reaction equation

HRID 345853 reaction equation
[I-].[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+]>C(OCC)C>[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

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 147210201-Phenyl-2-benzyl-3,4-dihydroisoquinolinium iodideHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 1-phenyl-2-benzyl-3,4-dihydroisoquinolinium iodide (1.0 g) in diethyl ether (10 ml) was added 3 M diethyl ether solution of methylmagnesium bromide (4.5 ml). The mixture was refluxed for 30 minutes with stirring and then poured into saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The separated organic layer was washed with water, sodium chloride aqueous solution and dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from n-hexane to give 1-methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline (0.64 g).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe separated organic layer was washed with water, sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-de46f78971d1459d81249f28b2e689fa
Source dataset
uspto-grants-1991_10
Patent number
US05059608

Reaction notes

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