HCID 22132535, compound → HCID 22132520, compound

HRID 1856791Notes

Reaction equation

HRID 1856791 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[Cu][C:17]#[N:18]>CN1CCCC1=O>[C:17]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1)#[N:18]

Participants

4

Reactant 2

HCID 22132535HCID 22132535, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22132520HCID 22132520, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 7-bromo-2-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline (12.0 g, 0.044 mol), copper (I) cyanide (8.7 g, 0.097 mol) and N-methyl-2-pyrrolidinone (100 ml) was heated at reflux for 4 h, cooled, then partitioned between dilute aqueous ammonia (500 ml) and ethyl acetate (300 ml). Organic phase was washed with dilute aqueous ammonia (100 ml), water (4×100 ml), then dried (Na2SO4) and evaporated in vacuo to give the title compound as an oil (7.89 g, 83%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperaturecooled
  4. custompartitioned between dilute aqueous ammonia (500 ml) and ethyl acetate (300 ml)
  5. washOrganic phase was washed with dilute aqueous ammonia (100 ml), water (4×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9ba3b1dc8c314032925ccae92a9fb14c
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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