Hydrochloric Acid → 2,3-Dihydro-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride

HRID 261476Notes

Reaction equation

HRID 261476 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]2([CH2:13][C:12]3[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:11]=3[O:10]2)[CH2:6][CH2:5]1)(=O)C.[ClH:21]>CCOCC>[ClH:21].[N+:18]([C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:7]3([CH2:6][CH2:5][NH:4][CH2:9][CH2:8]3)[CH2:13][C:12]=2[CH:14]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 127332352,3-Dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine]

Product 1

HCID 203942712,3-Dihydro-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.4 g of 2,3-dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine] in 150 ml of 6 N hydrochloric acid is refluxed for 45 hours and then stirred at ambient temperature for 16 hours. Thereafter, the reaction mixture is successively extracted once with ether, basified with 6 N sodium hydroxide and extracted thrice with ether. The combined ether extracts are dried and the solvent removed, leaving a yellow residue. The residue is dissolved in ether where it is converted to its hydrogen chloride salt. The salt is collected, dried and finally recrystallized twice from ethyl alcohol to give the product 2,3-dihydro-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride, mp 265°-266° C.

Workup

  1. extractionThereafter, the reaction mixture is successively extracted once with ether
  2. extractionextracted thrice with ether
  3. dry with materialThe combined ether extracts are dried
  4. customthe solvent removed
  5. customleaving a yellow residue
  6. customThe salt is collected
  7. customdried
  8. customfinally recrystallized twice from ethyl alcohol

Sources & evidence

ORD record
ord-122d54bf01484a2792bd4ac12456da3a
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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