1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone → HCID 18414318, compound

HRID 991494Notes

Reaction equation

HRID 991494 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[CH:4][CH:3]=1.[Cu][C:19]#[N:20]>CN1CCCC1=O>[C:19]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[CH:4][CH:3]=1)#[N:20]

Participants

4

Reactant 2

HCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 18414318HCID 18414318, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 7-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (51.7 g, 0.168 mol), copper (I) cyanide (31.8 g, 0.35 mol) and N-methyl-2-pyrrolidinone (620 ml) was heated at reflux for 4 h, cooled, then partitioned between dilute aqueous ammonia (1.5 L) and dichloromethane (5×300ml). The combined organic extracts were dried (Na2O4) and evaporated in vacuo to give the title compound (42.6 g, 100%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperaturecooled
  4. custompartitioned between dilute aqueous ammonia (1.5 L) and dichloromethane (5×300ml)
  5. customThe combined organic extracts were dried (Na2O4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d7d2877568ce4f6ea64f262e503497fb
Source dataset
uspto-grants-2002_10
Patent number
US06465485B1

Reaction notes

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