Hydrochloric Acid → HCID 12923065, compound

HRID 1589343Notes

Reaction equation

HRID 1589343 reaction equation
B#B.[CH2:3]([N:5]([CH:14]([CH3:27])[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:4].Cl>C1COCC1>[CH2:3]([N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]([CH3:27])[CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200Diboron2×HCID 23316739HCID 23316739, compound

Product 1

HCID 12923065HCID 12923065, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 500 ml 3-neck round bottom flask was fitted with a condenser and glass wool drying tube. The flask was charged with 60 ml of 1M diborane in THF and 7.7 g (0.022 mol) of N-ethyl-N-[1-methyl-4-(4-nitrophenyl)butyl]heptanamide in 50 ml of THF was added dropwise. The resulting reaction mixture was refluxed overnight and cooled. A solution of 25 ml of 2N hydrochloric acid was added dropwise in order to decompose any excess diborane. The mixture was evaporated under reduced pressure and an additional 150 ml of 2N hydrochloric acid was added. This mixture was refluxed for 1 hour, cooled and made basic with 5N sodium hydroxide. The mixture was extracted three times with diethyl ether and the organic phase was washed with water and a saturated sodium chloride solution. The organic phase was dried over sodium sulfate and evaporated to dryness to provide 7.389 g of N-ethyl-N-heptyl-α-methyl-4-nitrobenzenebutanamine as an oil.

Workup

  1. customA 500 ml 3-neck round bottom flask was fitted with a condenser
  2. customglass wool drying tube
  3. additionwas added dropwise
  4. customThe resulting reaction mixture
  5. temperaturewas refluxed overnight
  6. temperaturecooled
  7. customThe mixture was evaporated under reduced pressure
  8. additionan additional 150 ml of 2N hydrochloric acid was added
  9. temperatureThis mixture was refluxed for 1 hour
  10. temperaturecooled
  11. extractionThe mixture was extracted three times with diethyl ether
  12. washthe organic phase was washed with water
  13. dry with materialThe organic phase was dried over sodium sulfate
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-4a90ed8b22e7435c88a4a0827767ad19
Source dataset
uspto-grants-1986_02
Patent number
US04569801

Reaction notes

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