Water → HCID 68555817, compound

HRID 1804855Notes

Reaction equation

HRID 1804855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:18][CH3:19].[Cl:20]N1C(=O)CCC1=O.O.[OH-].[Na+]>CC(O)=O>[Cl:20][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([O:18][CH3:19])=[CH:4][C:5]=1[N:8]1[CH2:9][CH2:10][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 685538928-(4-Chloro-3-methoxyphenyl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 68555817HCID 68555817, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-(4-chloro-3-methoxyphenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.67 g, 5.89 mmol, Example 13, step 1) and 1-chloropyrrolidine-2,5-dione (0.786 g, 5.89 mmol) in AcOH (15 mL) was heated at 60° C. overnight. The mixture was cooled and water was added. Upon completion of addition, the mixture was neutralized with 1N NaOH, extracted with EtOAc, dried (Na2SO4), and concentrated to give 8-(2,4-dichloro-5-methoxyphenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.7 g, 5.34 mmol, 91% yield) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. additionUpon completion of addition
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ed24750daf544ffb9e95d1ba6049f47c
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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