Ammonia → HCID 18797048, compound

HRID 1003713Notes

Reaction equation

HRID 1003713 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:30])[C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][CH:19]=3)[CH2:9]2)=[CH:4][CH:3]=1.[Cu][C:32]#[N:33].N>CN1CCCC1=O>[C:32]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:30])[C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][CH:23]=3)[CH2:9]2)=[CH:4][CH:3]=1)#[N:33]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 18797025HCID 18797025, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 18797048HCID 18797048, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 7-Bromo-2-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (3.84 g, 8.3 mmol) and copper (I) cyanide (1.04 g, 11.4 mmol) in N-methyl-2-pyrrolidinone (20 ml) was heated at reflux for 1.5 h. The cooled mixture was poured onto 0.880 ammonia (50 ml) and crushed ice (~50 g) with stirring. The product was extracted into ethyl acetate (100 ml) and washed further with 0.880 ammonia (2×30 ml), then brine. Drying (Na2SO4) and evaporation of the solvent in vacuo afforded a brown oil. Chromatography on silica using 20-100% ethyl acetate-pentane gradient elution afforded the title compound as a colourless gum (1.58 g, 47%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. extractionThe product was extracted into ethyl acetate (100 ml)
  4. washwashed further with 0.880 ammonia (2×30 ml)
  5. customDrying
  6. custom(Na2SO4) and evaporation of the solvent in vacuo
  7. customafforded a brown oil
  8. washChromatography on silica using 20-100% ethyl acetate-pentane gradient elution

Sources & evidence

ORD record
ord-2ce85c17db01471b87b8034a71d04fd8
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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