Water → (E)-1-[3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-1-oxo-2-propenyl]piperidine

HRID 488148Notes

Reaction equation

HRID 488148 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:25]COC)=[C:6]([O:23][CH3:24])[CH:7]=[C:8]2/[CH:13]=[CH:14]/[C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])[CH3:2].O>CC(C)=O.Cl>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:25])=[C:6]([O:23][CH3:24])[CH:7]=[C:8]2/[CH:13]=[CH:14]/[C:15]([N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)=[O:16])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 14986472(E)-1-[3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-1-oxo-2-propenyl]piperidine

Product 1

HCID 14986482(E)-1-[3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-1-oxo-2-propenyl]piperidineYield 89.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

960 mg of (E)-1-[3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-1-oxo-2-propenyl]piperidine was dissolved in 50 ml of acetone, to which 1 ml of concentrated hydrochloric acid was gradually added at room temperature. After stirring at room temperature for 5 hours, the reaction mixture was slowly poured into water. The resultant crystals were collected by filtration, washed with water and dried to obtain 760 mg of the titled compound as yellow crystals.

Workup

  1. additionwas gradually added at room temperature
  2. filtrationThe resultant crystals were collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2b7b0b8b3b4a4007aa8f80804f8e2253
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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