Water → HCID 23316739, compound

HRID 1982478Notes

Reaction equation

HRID 1982478 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.[CH2:8]([NH:10][CH:11]([CH3:24])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH3:9].[C:25](Cl)(=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CC(C)=O>[CH2:8]([N:10]([CH:11]([CH3:24])[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)[C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 17313Heptanoyl chlorideHCID 23316732HCID 23316732, compound

Product 1

HCID 23316739HCID 23316739, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 500 ml 3-neck round bottom flask fitted with a thermometer and addition funnel was charged with 7.65 g of sodium carbonate and 70 ml of water. To this mixture was added 6.8 g (0.029 mol) of N-ethyl-α-methyl-4-nitrobenzenebutanamine and 70 ml of acetone. The resulting mixture was cooled to slightly below 25° C. and 4.5 ml (0.029 mol) of heptanoyl chloride and 70 ml of acetone were added while maintaining the temperature of the mixture in the range of about 20°-25° C. The suspension was stirred at room temperature overnight and evaporated to dryness under reduced pressure. The residue was slurried in water and extracted three times with diethyl ether. The organic extracts were combined, washed with water, 2N hydrochloric acid, twice with water and finally a saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to provide 7.723 g of N-ethyl-N-[1-methyl-4-(4-nitrophenyl)butyl]heptanamide as an oil.

Workup

  1. customA 500 ml 3-neck round bottom flask fitted with a thermometer and addition funnel
  2. temperatureThe resulting mixture was cooled to slightly below 25° C.
  3. temperaturewhile maintaining the temperature of the mixture in the range of about 20°-25° C
  4. customevaporated to dryness under reduced pressure
  5. extractionextracted three times with diethyl ether
  6. washwashed with water, 2N hydrochloric acid, twice with water
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-783d3c3d16954dde832e26048598a480
Source dataset
uspto-grants-1986_06
Patent number
US04596827

Reaction notes

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