Ethanol → HCID 12298151, compound

HRID 28158Notes

Reaction equation

HRID 28158 reaction equation
[ClH:1].Cl.[C:3]1([NH:9][C:10]2([C:23]([OH:25])=[O:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:31](O)[CH3:32]>>[ClH:1].[ClH:1].[C:3]1([NH:9][C:10]2([C:23]([O:25][CH2:31][CH3:32])=[O:24])[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 30172551-Benzyl-4-(phenylamino)piperidine-4-carboxylic acid dihydrochloride

Product 1

HCID 12298151HCID 12298151, compound

Procedure

A mixture of 19 parts of 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid dihydrochloride, 14.4 parts of sulfuric acid and 64 parts of ethanol is stirred and refluxed for 16 hours. The solvent is decanted. The residue is dissolved in water. The aqueous solution is alkalized with ammonium hydroxide and extracted with a mixture of methylbenzene and 2,2'-oxybispropane. The combined organic layers are dried over magnesium sulfate, filtered and evaporated. The oily residue is dissolved in 200 parts of 2,2'-oxybispropane and gaseous hydrogen chloride is introduced into the solution. The precipitated hydrochloride is filtered off, washed with 2-propanol, filtered off again and dried, yielding 11.5 parts of ethyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate dihydrochloride; mp. 212°-214.4° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. customThe solvent is decanted
  3. dissolutionThe residue is dissolved in water
  4. extractionextracted with a mixture of methylbenzene and 2,2'-oxybispropane
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe oily residue is dissolved in 200 parts of 2,2'-oxybispropane and gaseous hydrogen chloride
  9. additionis introduced into the solution
  10. filtrationThe precipitated hydrochloride is filtered off
  11. washwashed with 2-propanol
  12. filtrationfiltered off again
  13. customdried

Sources & evidence

ORD record
ord-10f78941a49940298f267a4eaa1004b8
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

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