Ammonium Chloride → 4,4-Dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 383993Notes

Reaction equation

HRID 383993 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:4][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 137285984,4-Dimethyl-1-phenyl-3,4-dihydroisoquinoline

Product 1

HCID 566869784,4-Dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinolineYield 4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 471 mg (2.0 mmol) of 4,4-dimethyl-1-phenyl-3,4-dihydroisoquinoline in MeOH (6 ml) was cooled to 0° C. and 151 mg (4.0 mmol) of NaBH4 were added in portions. After stirring for 3 h at RT a saturated aqueous NH4Cl solution was added. Then most of the methanol was removed under vacuum and the residue was extracted with EE. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 19 mg (0.08 mmol, 4%) of 4,4-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. additionwas added
  2. customThen most of the methanol was removed under vacuum
  3. extractionthe residue was extracted with EE
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-72e706a3014a4eb3aa429a5b55574ef3
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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