Nitric Acid → 2,3-Dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine]

HRID 261475Notes

Reaction equation

HRID 261475 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1)(=[O:7])[CH3:6].O>C(O)(=O)C>[C:5]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[C:19]([N+:1]([O-:4])=[O:2])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 127332342,3-Dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine]

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

3.8 g of nitric acid (sp gr 1.42) in 30 ml of glacial acetic acid is added dropwise to a stirred solution of 4.7 g of 2,3-dihydro-1'-acetylspiro[benzofuran-2,4'-piperidine] in 65 ml of glacial acetic acid. After total addition, the reaction mixture is slowly heated to 100° C. over a 2 hour span and then cooled and poured into 500 ml of water. The diluted mixture is extracted with chloroform and the chloroform extracts are washed sequentially with a saturated sodium bicarbonate solution, a saturated sodium chloride solution and then dried. The chloroform is removed under reduced pressure. The residue is triturated with ether causing an orange precipitate, which is collected and recrystallized first from an ethyl alcohol-ether mixture and then from ethyl alcohol to provide the product, 2,3-dihydro-1'-acetyl-5-nitrospiro[benzofuran-2,4'-piperidine], mp 149°-150° C.

Workup

  1. additionAfter total addition
  2. temperaturecooled
  3. extractionThe diluted mixture is extracted with chloroform
  4. washthe chloroform extracts are washed sequentially with a saturated sodium bicarbonate solution
  5. dry with materiala saturated sodium chloride solution and then dried
  6. customThe chloroform is removed under reduced pressure
  7. customThe residue is triturated with ether causing an orange precipitate, which
  8. customis collected
  9. customrecrystallized first from an ethyl alcohol-ether mixture

Sources & evidence

ORD record
ord-962b27478bb0484a82381b574ac38ac4
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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