Potassium Carbonate → HCID 13275586, compound

HRID 322127Notes

Reaction equation

HRID 322127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][NH:8][CH2:7][CH2:6]2.Br[CH2:16][CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O1CCOCC1.[I-].[K+]>[C:18]([CH2:17][CH2:16][N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:9]1)#[N:19]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 170203-Bromopropionitrile

Product 1

HCID 13275586HCID 13275586, compoundYield 84.9%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9.20 g, 40.1 mmol, 1.00 equiv, Aldrich), 3-bromopropionitrile (3.66 mL, 44.1 mmol, 1.10 equiv, Aldrich), potassium carbonate (33.25 g, 240.6 mmol, 6.00 equiv), and potassium iodide (266 mg, 1.60 mmol, 0.04 equiv) in n-butanol (70 mL) and 1,4-dioxane (70 mL) was stirred at reflux under argon for 48 hours. The mixture was cooled to room temperature and concentrated. The residue was purified by flash chromatography (SiO2, MeOH—EtOAc 0:1 to 1:19) to afford 8.39 g of white solid (59%), which was characterized spectroscopically.

Workup

  1. temperatureat reflux under argon for 48 hours
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (SiO2, MeOH—EtOAc 0:1 to 1:19)

Sources & evidence

ORD record
ord-0452a53fc36146a9a216d37f378d632e
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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