1,2,3,4-Tetrahydroisoquinoline → 3,4-Dihydroisoquinoline

HRID 1173116Notes

Reaction equation

HRID 1173116 reaction equation
BrN1C(=O)CCC1=O.[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1.[OH-].[Na+]>C(Cl)Cl>[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][N:10]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

Product 1

HCID 767053,4-DihydroisoquinolineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (39.2 g) was added to a methylene chloride solution (300 ml) containing 26.67 g (0.2 mol) of 1,2,3,4-tetrahydroisoquinoline under ice-cooling over 20 minutes. After stirring for 40 minutes, an aqueous 30% sodium hydroxide solution (130 ml) was added to the reaction solution. The organic layer was washed with water and then extracted with a 10% aqueous hydrochloric acid (200 ml). The aqueous layer was washed with methylene chloride, basified with an aqueous ammonia, and then extracted with methylene chloride. The extract was dried over magnesium sulfate and then evaporated. The resulting residue was distilled (about 16 mmHg, 120° C.), to give 21.5 g of the title compound as an oil.

Workup

  1. temperaturecooling over 20 minutes
  2. washThe organic layer was washed with water
  3. extractionextracted with a 10% aqueous hydrochloric acid (200 ml)
  4. washThe aqueous layer was washed with methylene chloride
  5. extractionextracted with methylene chloride
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated
  8. distillationThe resulting residue was distilled (about 16 mmHg, 120° C.)

Sources & evidence

ORD record
ord-8d9e50ec41eb4c4591c116bf2dfbf13f
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

Loading…