N-Methoxy-N-methylbenzamide → HCID 18185371, compound

HRID 1358604Notes

Reaction equation

HRID 1358604 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:4].C([Li])CCC.CON(C)[C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.CCCCCC>[C:29]([C:7]1[CH:8]=[C:9]([N:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)[CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:20])([CH3:19])[CH3:1])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 569575N-Methoxy-N-methylbenzamideHCID 645096HCID 645096, compoundHCID 178418339Butyllithium

Product 1

HCID 18185371HCID 18185371, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 1.375 g (5 mmol) of 2,2-dimethyl-N-[4-(4-methyl-piperazin-1-yl)-phenyl]-propionamide was dissolved in 25 ml tetrahydrofuran and cooled to −70° C. Under argon 7.8 ml (12.5 mmol) of a 1.6 M n-butyl lithium solution in hexane was added slowly at this temperature. The cooling bath was removed and the mixture was stirred for 3 h at room temperature. The reaction mixture was cooled down again to −70° C. and a solution of 1.234 g N-methoxy-N-methyl benzamide (7.2 mmol) in 5 ml tetrahydrofuran was added slowly at −70° C. After 10 min the cooling bath was removed and stirring was continued at room temperature for 1 hour. Water (50 ml) was added to quench the reaction and the mixture was extracted with diethylether (three times 50 ml). The organic layer was dried with magnesium sulfate and evaporated to give a brown oil, which was purified by flash chromatography with dichloromethane/methanol to yield 315 mg (17%)of the product as a light orange solid.

Workup

  1. customThe cooling bath was removed
  2. temperatureThe reaction mixture was cooled down again to −70° C.
  3. customAfter 10 min the cooling bath was removed
  4. stirringstirring
  5. waitwas continued at room temperature for 1 hour
  6. additionWater (50 ml) was added
  7. customto quench
  8. customthe reaction
  9. extractionthe mixture was extracted with diethylether (three times 50 ml)
  10. dry with materialThe organic layer was dried with magnesium sulfate
  11. customevaporated
  12. customto give a brown oil, which
  13. customwas purified by flash chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-a2befd4f4bf54ac188b95febdb1b99dd
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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