3,4-Dimethoxyphenol → HCID 10825289, compound

HRID 851189Notes

Reaction equation

HRID 851189 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.O=[C:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH:15]1[C:20](OCC)=[O:21]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]=3[C:20](=[O:21])[O:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 162513,4-DimethoxyphenolHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 10825289HCID 10825289, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Prepared by the method described in Example 1 except that the 3,4-dimethoxyphenol (61.5 g, 0.40 moles) is added in one portion to an ice-cooled mixture of ethyl 4-oxo-3-piperidinecarboxylate hydrochloride (75 g, 0.36 moles) and 200 ml of 72% sulfuric acid. Recrystallization from acetonitrile yielded the product (71 g), mp 186°-188° C.

Workup

  1. customPrepared by the method
  2. temperaturecooled
  3. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-846a71034a5f43e7961b9b06209e78a8
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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