Hydrochloric Acid → HCID 21405556, compound

HRID 972811Notes

Reaction equation

HRID 972811 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH3:9])[CH2:3]1.[N+:10]([C:13]1[CH:14]=[C:15]2[C:20](=O)[O:19][C:17](=[O:18])[C:16]2=[CH:22][CH:23]=1)([O-:12])=[O:11].Cl>C(Cl)(Cl)Cl.C(O)(C)C>[CH2:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([N:1]2[C:20](=[O:19])[C:15]3=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:23][CH:22]=[C:16]3[C:17]2=[O:18])[CH2:3]1)[CH3:9]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 980943-amino-N-ethylpiperidineHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 21405556HCID 21405556, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent2×

Procedure

6.40 Grams of 3-amino-1-ethylpiperidine in 150 milliliters of chloroform were added to a suspension of 9.65 grams of 4-nitrophthalic anhydride in 100 milliliters of chloroform. The solution formed was stirred at room temperature for twenty minutes and evaporated to dryness. The gummy residue was dissolved in 50 milliliters of acetic anhydride and the mixture was heated to 100° C. for thirty-five minutes. The excess acetic anhydride was distilled and the residue extracted into 100 milliliters of chloroform and the solution was washed with 50 milliliters of saturated sodium bicarbonate solution, 50 milliliters of water, dried over magnesium sulphate and evaporated to give a brown oil. The oil was dissolved in 20 milliliters of isopropanol and ethereal hydrogen chloride was added to give 9.33 grams of the title compound as the hydrochloride, quarterhydrate.

Workup

  1. customThe solution formed
  2. customevaporated to dryness
  3. dissolutionThe gummy residue was dissolved in 50 milliliters of acetic anhydride
  4. temperaturethe mixture was heated to 100° C. for thirty-five minutes
  5. distillationThe excess acetic anhydride was distilled
  6. extractionthe residue extracted into 100 milliliters of chloroform
  7. washthe solution was washed with 50 milliliters of saturated sodium bicarbonate solution, 50 milliliters of water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customto give a brown oil

Sources & evidence

ORD record
ord-0fa7363d25474fdaa4462596aa319e73
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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