Ethanol → ethyl 1-benzyl-4-hydroxypiperidine-4-carboxylate

HRID 1085722Notes

Reaction equation

HRID 1085722 reaction equation
S(=O)(=O)(O)O.Cl.[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([C:21]#N)([OH:20])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[OH:24].[Na+].[CH2:28]([OH:30])[CH3:29]>>[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([C:21]([O:30][CH2:28][CH3:29])=[O:24])([OH:20])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 27237801-Benzyl-4-hydroxypiperidine-4-carbonitrile monohydrochloride

Product 1

HCID 272010ethyl 1-benzyl-4-hydroxypiperidine-4-carboxylate

Conditions

Temperature
130 °C

Procedure

Conc. sulfuric acid (12 ml) was added to an ethanol solution (50 ml) of 1-benzyl-4-cyano-4-hydroxypiperidine hydrochloride (10 g) and the resulting mixture was heated at 130° C. for 24 hours in a sealed tube. After concentration of the reaction mixture, ice water was added to the concentrate. The resulting mixture was added with an aqueous solution of sodium hydrogencarbonate. After adjusting the thus-obtained solution to pH 7.0, it was extracted with diethyl ether. The extract was washed with brine and then added with anhydrous sodium sulfate to dry the same. The solvent was distilled off to obtain the intended product (9.7 g).

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe extract was washed with brine
  3. additionadded with anhydrous sodium sulfate
  4. customto dry the same
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-edcb30e474d14f59a19d8f2a61af3835
Source dataset
uspto-grants-1991_04
Patent number
US05010188

Reaction notes

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