Sodium Carbonate → HCID 19045339, compound

HRID 1781396Notes

Reaction equation

HRID 1781396 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]2[CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15][CH2:14]2)=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>Cl.O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][C:16](=[O:17])[CH2:21][CH2:22]2)=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 19045440HCID 19045440, compound

Product 1

HCID 19045339HCID 19045339, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 5.24 g (15.0 mmol) of 1-(8-[2-(4-acetamido-3-nitrophenyl)ethyl]-1,4-dioxa-8-azaspiro[4.5]decane in 30 mL 2N hydrochloric acid was heated at reflux for 1.5 hours. The cooled mixture was basified (pH 9-10) with saturated sodium carbonate solution and 10N sodium hydroxide, diluted with 100 ml water, and extracted with methylene chloride (3×150 ml). The extract was washed with 50 ml water and brine, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to give 3.95 g (100%) of 1-[2-(4-amino-3-nitrophenyl)ethyl]-4-piperidone as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. extractionextracted with methylene chloride (3×150 ml)
  4. washThe extract was washed with 50 ml water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7ff27640a0d54d469b56503d444125ed
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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