Ammonia → HCID 22626862, compound

HRID 277892Notes

Reaction equation

HRID 277892 reaction equation
C(OC([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12](Br)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.[Cu][C:22]#[N:23].N.O>CN1CCCC1=O>[C:22]([C:12]1[CH:11]=[C:10]2[C:15]([C:16]([CH3:18])([CH3:19])[CH2:17][NH:8][CH2:9]2)=[CH:14][CH:13]=1)#[N:23]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 226268611,1-Dimethylethyl 7-bromo-3,4-dihydro-4,4-dimethyl-2(1H)-isoquinolinecarboxylateHCID 178418546HCID 178418546, compound

Product 1

HCID 22626862HCID 22626862, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of N-tert-butyloxycarbonyl-7-bromo-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline (4.2 g, 0.01236 mol) and copper (I) cyanide (2.2 g, 0.0247 mol) in N-methylpyrrolidinone (120 ml) was heated at vigorous reflux for 2 hours. On cooling the mix was poured into 0.880 ammonia (300 ml) and water (300 ml) and extracted into ethyl acetate (4×200 ml). Combined organic extracts were washed with 1:10.880 ammonia:water (3×150 ml), water (3×200 ml) and brine (150 ml) and dried (Na2SO4). Solvent was removed in vacuo to afford the title compound as a pale brown solid (1.99 g, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat vigorous reflux for 2 hours
  3. temperatureOn cooling the mix
  4. extractionextracted into ethyl acetate (4×200 ml)
  5. washCombined organic extracts were washed with 1:10.880 ammonia
  6. dry with materialwater (3×150 ml), water (3×200 ml) and brine (150 ml) and dried (Na2SO4)
  7. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-ecabe6565e7a4914a5a283502308777b
Source dataset
uspto-grants-2002_03
Patent number
US06358974B1

Reaction notes

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