Hydrochloric Acid → HCID 23316732, compound

HRID 1982477Notes

Reaction equation

HRID 1982477 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13](=O)[CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH2:17]([NH2:19])[CH3:18].C([BH3-])#N.[Na+].Cl>CO>[CH2:17]([NH:19][CH:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11198Ethylamine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 23316746HCID 23316746, compound

Product 1

HCID 23316732HCID 23316732, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 300 ml round bottom flask fitted with a calcium sulfate drying tube was charged with 6.681 g (0.0322 mol) of 5-(4-nitrophenyl)-2-pentanone in 100 ml of methanol. This mixture was charged with 13.2 g (0.161 mol) of ethylamine hydrochloride and 2.03 g (0.0322 mol) of sodium cyanoborohydride. The resulting suspension was stirred at room temperature over the weekend (about 72 hours) and acidified with concentrated hydrochloric acid. The volatiles were evaporated under reduced pressure and 300 ml of water was added to the residue. The mixture was extracted twice with diethyl ether and the organic phase was washed with water and a saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness. This material was discarded. The aqueous phase was basified with 5N sodium hydroxide and extracted three times with diethyl ether. The organic extracts were combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 6.838 g of N-ethyl-α-methyl-4-nitrobenzenebutanamine.

Workup

  1. customA 300 ml round bottom flask fitted with a calcium sulfate drying tube
  2. customThe volatiles were evaporated under reduced pressure and 300 ml of water
  3. additionwas added to the residue
  4. extractionThe mixture was extracted twice with diethyl ether
  5. washthe organic phase was washed with water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. extractionextracted three times with diethyl ether
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. customEvaporation of the solvent

Sources & evidence

ORD record
ord-12760eecb9dd4ae0996b24c9815720ef
Source dataset
uspto-grants-1986_06
Patent number
US04596827

Reaction notes

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