Hydrochloric Acid → HCID 5744998, compound

HRID 483796Notes

Reaction equation

HRID 483796 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].[CH2:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][Cl:25])[CH3:19].C([O-])([O-])=O.[Na+].[Na+].Cl>C(#N)C>[ClH:25].[CH2:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:9]1[CH2:8][CH2:7][C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:11][CH2:10]1)[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 32414NormeperidineHCID 5208211-Chloro-4-ethoxybutane

Product 1

HCID 5744998HCID 5744998, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C.

Workup

  1. temperatureunder reflux
  2. filtrationThe mixture was filtered
  3. customthe solvent removed
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washthe solution washed with water
  6. dry with materialdried (MgSO4)
  7. customDestillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg
  8. custom3062 (1958) 180° C./1 mm Hg

Sources & evidence

ORD record
ord-f9d1676c42964943926696a83eab1022
Source dataset
uspto-grants-1993_07
Patent number
US05227389

Reaction notes

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