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

HRID 261506Notes

Reaction equation

HRID 261506 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 hydrochoric 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 is 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 is 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-542513ba06184051839d480704a114b4
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

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