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

HRID 1395471Notes

Reaction equation

HRID 1395471 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.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(O)(C)(C)C>[N:26]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])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

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

Product 1

HCID 127961954-(6-Piperidinohexyl)3,5-dioxomorpholine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of 19.6 grams (53.2 millimoles) of 6-(3,5-dioxomorpholino)hexyl p-toluenesulfonate in 54 milliliters of tertiary butyl alcohol was added 5.3 milliliters of tertiary (53 millimoles) of piperidine in 54 milliliters of tertiary butyl alcohol. The reaction mixture was heated at reflux temperature for about 22 hours to obtain 4-(6-piperidinohexyl)-3,5-dioxomorpholine.p-toluenesulfonate product which crystallized from tertiary butyl alcohol-ether mixture in a yield of 13.45 grams (56 percent) as an off-white solid, m.p. 125°-128° C. A portion of this product after purification by (a) chromatographing on Silicar CC4 Special (Silica gel, product of Mallinkrodt) employing 10:1 dichloromethanemethanol as eluant, (b) recovering from the effluent and (c) recrystallizing from tertiary butyl alcohol-ether, was a white solid, m.p. 121°-122.5° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for about 22 hours

Sources & evidence

ORD record
ord-928b0a7152c54d7eab6689b028c95ffb
Source dataset
uspto-grants-1980_05
Patent number
US04203991

Reaction notes

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