Hydrochloric Acid → HCID 5744998, compound

HRID 2379034Notes

Reaction equation

HRID 2379034 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-352ed2c999c145d39e93b1de8b9e9709
Source dataset
uspto-grants-1994_11
Patent number
US05360805

Reaction notes

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