Diethyl Ether → HCID 70578049, compound

HRID 1413948Notes

Reaction equation

HRID 1413948 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)=[O:2].COS([O:27][CH3:28])(=O)=O.[CH2:29]([NH2:31])[CH3:30].[OH-:32].[Na+].CC[O:36][CH2:37]C>C(Cl)Cl>[OH2:2].[C:28]([OH:27])(=[O:36])[C:1]([OH:2])=[O:32].[C:10]1([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]2[CH2:7][CH2:8][N:3]([CH:1]=[N:31][CH2:29][CH3:30])[CH2:4][CH2:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:10]1([CH:9]([CH:6]2[CH2:7][CH2:8][N:3]([CH:1]=[N:31][CH2:29][CH3:30])[CH2:4][CH2:5]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:28]([OH:27])(=[O:2])[C:37]([OH:36])=[O:32]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6341EthylamineHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 13093871HCID 13093871, compound

Product 1

HCID 70578049HCID 70578049, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.00 g (0.029 mole) of N-formyl-4-diphenylmethylpiperidine and 3.61 g (2.67 ml, 0.029 mole) of dimethylsulfate was heated on a steam bath for two hours to give a clear thick syrup. To this material was then added 1.38 g (2.00 ml, 0.031 mole) of ethylamine in 15 ml of methylene chloride. The resulting solution was stirred for 1.5 hours at 25°, stripped, slurried in ether, and treated with 28 ml of 3 N sodium hydroxide solution. The ethereal layer was dried over potassium carbonate, filtered through diatomaceous earth filter aid and evaporated to give 8.77 g of yellow liquid. Treatment of this material in isopropanol with 3.26 g of oxalic acid dihydrate afforded 5.0 g of white solid m.p. 165°-175° C. Recrystallization from isopropanol afforded pure 4-(diphenylmethyl)-1-N-ethyliminomethylpiperidine oxalate hemihydrate as a white solid; m.p. 185°-187° C.

Workup

  1. temperaturewas heated on a steam bath for two hours
  2. customto give a clear thick syrup
  3. dry with materialThe ethereal layer was dried over potassium carbonate
  4. filtrationfiltered through diatomaceous earth
  5. filtrationfilter aid
  6. customevaporated

Sources & evidence

ORD record
ord-c56645d9fe114544b2e2597143aa919f
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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