Water → 1,2,3,4-Tetrahydroisoquinoline-6-carbonitrile

HRID 2080764Notes

Reaction equation

HRID 2080764 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7](C(=O)C(F)(F)F)[CH2:6][CH2:5]2.O.O.[NH4+].[CH3:21][N:22]1C(=O)CCC1>>[CH2:8]1[C:9]2[C:4](=[CH:3][C:2]([C:21]#[N:22])=[CH:11][CH:10]=2)[CH2:5][CH2:6][NH:7]1

Participants

5

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 22024077Azanium;hydrateHCID 231554111-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 102410651,2,3,4-Tetrahydroisoquinoline-6-carbonitrile

Procedure

The compound (2.23 g) obtained in Example 17-2 was dissolved in NMP (27 ml) and added with cuprous cyanide (1.56 g) and the whole was refluxed under heating for 4 hours. After completion of the reaction, the whole was cooled with ice and added with water and ammonium water. The resultant was subjected to extraction with chloroform and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The resultant was dissolved in diethyl ether and added with a 4 mol/l hydrogen chloride/dioxane solution. The precipitate was filtrated and washed with diethylether. The resultant was dried under heating, thereby obtaining a hydrochloride (1.95 g) of the subject compound as a brown solid.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 4 hours
  3. customAfter completion of the reaction
  4. temperaturethe whole was cooled with ice
  5. extractionThe resultant was subjected to extraction with chloroform
  6. dry with materialdried with magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. dissolutionThe resultant was dissolved in diethyl ether
  9. additionadded with a 4 mol/l hydrogen chloride/dioxane solution
  10. filtrationThe precipitate was filtrated
  11. washwashed with diethylether
  12. customThe resultant was dried
  13. temperatureunder heating

Sources & evidence

ORD record
ord-e7bfc4c124ed4374a8f0b48dc4b7d156
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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