Hydrochloric Acid → HCID 19045345, compound

HRID 1781360Notes

Reaction equation

HRID 1781360 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]2([CH2:17][C:16]3[C:11](=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[CH:14][CH:15]=3)[C:10]2=[O:21])[CH2:6][CH2:5]1)(=O)C.[ClH:22]>C(O)C>[ClH:22].[N+:18]([C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][C:7]3([C:10]2=[O:21])[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)=[CH:15][CH:14]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 190455381′-Acetyl-6-nitrospiro[2H-indene-2,4′-piperidin]-1(3H)-one

Product 1

HCID 19045345HCID 19045345, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.216 g (0.75 mmol) 1'-acetyl-1,3-dihydro-1-oxo-6-nitrospiro[2H-indene-2,4'-piperidine] and 2 ml (6 mmol) 3N hydrochloric acid in 6 ml ethanol was heated at reflux for 18 hours. Another 0.2 ml (0.6 mmol) 3N hydrochloric acid was added and the solution was heated at reflux for 4 hours, then cooled to room temperature to give a white precipitate. The precipitate was filtered off, washed with ethanol, and dried to give 0.158 g (74%) product; 1H NMR (DMSO-d6): δ1.60 (d, 2H), 1.96 (m, 2H), 3.06 (m, 2H), 3.3 (m, 4H), 7.88 (d, 1H), 8.35 (d, 1H), 8.55 (d of d, 1H), 8.9 (broad s, 2H).

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturethe solution was heated
  3. temperatureat reflux for 4 hours
  4. customto give a white precipitate
  5. filtrationThe precipitate was filtered off
  6. washwashed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-5dfbaed87b85463b84e1def719b9b3e4
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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