1-Heptanamine, N-ethyl- → HCID 13561098, compound

HRID 1982474Notes

Reaction equation

HRID 1982474 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[CH2:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:23]>C(Cl)(Cl)(Cl)Cl.C(OCC)C.O>[CH2:22]([N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:23]

Participants

7

Reactant 3

HCID 480381-Heptanamine, N-ethyl-HCID 65578Oxalyl chlorideHCID 797114-(4-Nitrophenyl)butyric acid

Product 1

HCID 13561098HCID 13561098, compoundYield 128%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

A 500 ml round bottom flask fitted with an addition funnel and a calcium sulfate drying tube was charged with 8.0 g (0.03 mol) of 4-(4-nitrophenyl)butyric acid in 180 ml of carbon tetrachloride. To this stirred solution was added 16.5 ml (0.19 mol) of oxalyl chloride dropwise. The addition funnel was removed and a condenser was fitted onto the flask. The reaction mixture was refluxed for 3 hours, cooled and the excess oxalyl chloride was evaporated under reduced pressure. Approximately 100 ml of dry diethyl ether was added to the solution which was subsequently cooled in ice. To this cooled solution was added 16.3 g (0.115 mol) of ethylheptylamine dissolved in approximately 60 ml of diethyl ether. The resulting reaction mixture was stirred at room temperature overnight and diluted with a mixture of water and diethyl ether. The aqueous phase was separated and further extracted three times with diethyl ether. The organic extracts were combined, washed with water, hydrochloric acid, water (2×), a 10% aqueous sodium carbonate solution and a saturated sodium chloride solution. The organic phase was separated, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to provide 12.847 g of N-ethyl-N-heptyl-4-nitrobenzenebutanamide as an oil.

Workup

  1. customA 500 ml round bottom flask fitted with an addition funnel and a calcium sulfate drying tube
  2. customThe addition funnel was removed
  3. customa condenser was fitted onto the flask
  4. temperatureThe reaction mixture was refluxed for 3 hours
  5. temperaturecooled
  6. customthe excess oxalyl chloride was evaporated under reduced pressure
  7. additionApproximately 100 ml of dry diethyl ether was added to the solution which
  8. temperaturewas subsequently cooled in ice
  9. customThe resulting reaction mixture
  10. customThe aqueous phase was separated
  11. extractionfurther extracted three times with diethyl ether
  12. washwashed with water, hydrochloric acid, water (2×)
  13. customThe organic phase was separated
  14. dry with materialdried over anhydrous sodium sulfate
  15. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1e3d46443cc441d1ad7c9df1882c0519
Source dataset
uspto-grants-1986_06
Patent number
US04596827

Reaction notes

Loading…