Hydrogen Bromide → 1,2,3,4-Tetrahydroisoquinolin-6-ol--hydrogen bromide (1/1)

HRID 1585237Notes

Reaction equation

HRID 1585237 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[BrH:13]>>[BrH:13].[CH2:9]1[C:10]2[C:5](=[CH:4][C:3]([OH:2])=[CH:12][CH:11]=2)[CH2:6][CH2:7][NH:8]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 133617991,2,3,4-Tetrahydroisoquinolin-6-ol--hydrogen bromide (1/1)

Procedure

A solution of 8.00 g (49 mmol) of 6-Methoxy-1,2,3,4-tetrahydro-isoquinoline in 196 mL of 48% hydrobromic acid was refluxed for 3 h. The mixture was then concentrated and coevaporated several times with ethanol. The resulting slurry was filtered and dried under vacuum to give 7.43 g of 1,2,3,4-Tetrahydro-isoquinolin-6-ol hydrobromide as a solid. To 7.38 g of the crude hydrobromide dissolved in 117 mL each of dioxane and water was added 6.34 g (35.3 mmol) of benzyl chloroformate with ice bath cooling. A 1 M solution of potassium carbonate was slowly added until a pH of 10 was maintained. The mixture was stirred overnight at room temperature. Excess dioxane was removed by evaporation, and the resulting aqueous mixture was acidified with 1 N HCl and the product extracted with ethyl acetate. The organic portion was washed with water and brine, dried over Na2SO4 and concentrated to give 10.4 g of an oil which was crystallized from ether/hexane to give 7.05 g of 7D as a solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. filtrationThe resulting slurry was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fc0deb0de5824e509237ea8afa2f6f9c
Source dataset
uspto-grants-1999_08
Patent number
US05936089

Reaction notes

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