Dimethylformamide → HCID 56933724, compound

HRID 881993Notes

Reaction equation

HRID 881993 reaction equation
S([CH2:11][CH:12]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13](=[CH2:19])[CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[O:47][CH3:48])[CH2:43][NH:42][CH2:41][CH2:40]2>O>[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[O:47][CH3:48])[CH2:43][N:42]([CH2:11][CH:12]([C:13]([CH2:14][Si:15]([CH3:16])([CH3:18])[CH3:17])=[CH2:19])[CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:41][CH2:40]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 156236,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline2×HCID 86691333HCID 86691333, compound2×

Product 1

HCID 56933724HCID 56933724, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(3-(tosylmethyl)-5-methyl-2-methylenehexyl)trimethylsilane (Formula 4; 72.0 mg, 0.195 mmol) and Na2CO3 (41.4 mg, 0.391 mmol) were added to DMF (2 mL). Then, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (Formula 3; 75.4 mg, 0.391 mmol) was added thereto, and the mixture was heated up to 80° C. and stirred for 30 hr. Distilled water was put into the reaction solution to complete the reaction, and then the temperature was increased to normal temperature. An organic layer was extracted, the organic layer collected was washed with distilled water and a brine solution, and the remaining solvent was distilled under reduced pressure. Anhydrous magnesium sulfate was used to dry the organic layer, filtration under reduced pressure and evaporation under reduced pressure were performed, and then column chromatography was used to obtain 53.3 mg (yield 75%) of the title compound.

Workup

  1. customthe reaction
  2. temperaturethe temperature was increased to normal temperature
  3. extractionAn organic layer was extracted
  4. customthe organic layer collected
  5. washwas washed with distilled water
  6. distillationa brine solution, and the remaining solvent was distilled under reduced pressure
  7. customto dry
  8. filtrationthe organic layer, filtration
  9. customunder reduced pressure and evaporation under reduced pressure

Sources & evidence

ORD record
ord-f632e2cf6145427eb19bb628fb18c6fc
Source dataset
uspto-grants-2015_03
Patent number
US08993766B2

Reaction notes

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