Sodium Carbonate → 4-(Ethylenedioxy)-1-(diphenylacetyl)piperidine

HRID 1449053Notes

Reaction equation

HRID 1449053 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23]1[CH2:32][O:31][CH:30]2[CH:25]([CH2:26][CH2:27][NH:28][CH2:29]2)[O:24]1>C1C=CC=CC=1>[CH2:23]1[CH2:32][O:31][CH:30]2[CH:25]([CH2:26][CH2:27][N:28]([C:8](=[O:9])[CH:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:29]2)[O:24]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 746372,2-Diphenylacetyl chlorideHCID 69545778Octahydro-[1,4]dioxino[2,3-c]pyridine

Product 1

HCID 705946584-(Ethylenedioxy)-1-(diphenylacetyl)piperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 24 parts of diphenylacetyl chloride in 250 parts by volume of benzene is added 15 parts of solid sodium carbonate and 16.4 parts of 4-(ethylenedioxy)piperidine. The resultant mixture is refluxed for about 29 hours, left overnight at room temperature, and filtered. The filtrate is washed twice with 10% hydrochloric acid, twice with saturated sodium bicarbonate solution and once with brine. The filtrate is then dried over magnesium sulfate, concentrated and recrystallized from cyclohexane to afford 4-(ethylenedioxy)-1-(diphenylacetyl)piperidine, melting at about 136°-137° C. This compound has the following structural formula ##STR20##

Workup

  1. filtrationfiltered
  2. washThe filtrate is washed twice with 10% hydrochloric acid, twice with saturated sodium bicarbonate solution and once with brine
  3. dry with materialThe filtrate is then dried over magnesium sulfate
  4. concentrationconcentrated
  5. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-cc7e1189931c4a8b99bd5caf8accbfd3
Source dataset
uspto-grants-1980_02
Patent number
US04188485

Reaction notes

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