Piperidine → 4-(6-Piperidinohexyl)3,5-dioxomorpholine

HRID 127726Notes

Reaction equation

HRID 127726 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:22](=[O:23])[CH2:21][O:20][CH2:19][C:18]2=[O:24])(=O)=O)=CC=1.[H-].[Li+].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>COCCOC>[N:28]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:18](=[O:24])[CH2:19][O:20][CH2:21][C:22]2=[O:23])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 62714Lithium hydrideHCID 127961946-(3,5-Dioxomorpholino)hexyl p-toluenesulfonate

Product 1

HCID 127961954-(6-Piperidinohexyl)3,5-dioxomorpholineYield 42.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a mixture of 3.63 grams (9.84 millimoles) of 6-(3,5-dioxomorpholino)hexyl p-toluenesulfonate (prepared as described in Example IX) and 84.75 milligrams (10.7 millimoles) of lithium hydride in 10 milliliters of 1,2-dimethoxyethane was added 1.0 milliliter (10.0 millimoles) of piperidine in 10 milliliters of 1,2-dimethoxyethane. The mixture was heated under reflux for 22 hours, and the resulting heterogeneous mixture filtered to obtain a clear yellow filtrate. The filtrate was concentrated to an orange oil which after evaporative distillation (bath 120° C.; 0.05 torr.) produced 1.18 grams (42.5 percent yield) of 4-(6-piperidinohexyl)-3,5-dioxomorpholine base having infrared and nuclear magnetic resonance spectral characteristics appropriate for said compound. A 286.23 milligram (1.02 millimoles) sample of the free base, 4-(6-piperidinohexyl)-3,5-dioxomorpholine, was dissolved in 1.0 milliliter of 1 N sodium hydroxide (1.0 millimole) and the mixture concentrated to produce 289.63 grams (90 percent yield) of sodium [2-(6-piperidinohexyl)-amino-2-oxoethoxy]acetate product with the following spectral characteristics;

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 22 hours
  3. filtrationthe resulting heterogeneous mixture filtered
  4. customto obtain a clear yellow filtrate
  5. concentrationThe filtrate was concentrated to an orange oil which
  6. distillationafter evaporative distillation (bath 120° C.; 0.05 torr.)

Sources & evidence

ORD record
ord-be0e903cfb3a4db6949270a8fcd1d2c7
Source dataset
uspto-grants-1981_03
Patent number
US04256891

Reaction notes

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