Gamma-Valerolactone → HCID 67829744, compound

HRID 1198146Notes

Reaction equation

HRID 1198146 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[C:9]1(=[O:15])O[CH:12]([CH3:13])[CH2:11][CH2:10]1.C(=O)([O-])[O-:17].[K+].[K+].[C:22]([O-:27])(=[O:26])[C:23]([O-:25])=[O:24]>C(Cl)Cl.O>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[OH:17][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1)=[O:15]

Participants

7

Reactant 4

HCID 7921Gamma-ValerolactoneHCID 11430Potassium CarbonateHCID 71081OxalateHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 67829744HCID 67829744, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5.3 g. (0.05 mole) 4-amino-1-methylpiperidine are heated with 5.4 ml. (0.06 mole) γ-valerolactone for 48 hours at 90° C. The reaction mixture is dissolved in 50 ml. water and shaken up with methylene chloride. The aqueous phase is rendered alkaline with potassium carbonate and extracted with n-butanol. The crude base is dissolved in ethanol, 3 g. oxalic acid are added thereto, insolubles are filtered off and the filtrate is distilled off. There are obtained 8.5 g. of the oxalate of the title compound in the form of a viscous, semi-solid product. Yield 56% of theory.

Workup

  1. dissolutionThe reaction mixture is dissolved in 50 ml
  2. extractionextracted with n-butanol
  3. dissolutionThe crude base is dissolved in ethanol
  4. additionoxalic acid are added
  5. filtrationinsolubles are filtered off
  6. distillationthe filtrate is distilled off
  7. customThere are obtained 8.5 g

Sources & evidence

ORD record
ord-ffc6e723d780467a86cf7860ddf18281
Source dataset
uspto-grants-1994_01
Patent number
US05280031

Reaction notes

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