Hydrochloric Acid → 2,3-Dihydro-1'-[3-(4-fluorobenzoyl)propyl]-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride

HRID 261477Notes

Reaction equation

HRID 261477 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:16][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][C:8]=2[CH:17]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C1O[C:29]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)([CH2:30][CH2:31][CH2:32][Cl:33])[O:28]C1.Cl.[OH-].[Na+]>C(O)CCC.CO>[ClH:33].[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:29]([CH2:30][CH2:31][CH2:32][N:13]2[CH2:12][CH2:11][C:10]3([CH2:9][C:8]4[CH:17]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=4[O:16]3)[CH2:15][CH2:14]2)=[O:28])=[CH:39][CH:38]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 127332362,3-Dihydro-5-nitrospiro[benzofuran-2,4'-piperidine]

Product 1

HCID 203943172,3-Dihydro-1'-[3-(4-fluorobenzoyl)propyl]-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

A stirred suspension of 5.2 g of 2,3-dihydro-5-nitrospiro[benzofuran-2,4'-piperidine] free base of C, 7.0 g of potassium carbonate, a few grains of potassium iodide and 6.2 g of γ-chloro-p-fluorobutyrophenone ethylene ketal in 200 ml of n-butyl alcohol is refluxed for 24 hours. Thereafter, the reaction mixture is permitted to cool to ambient temperature and then filtered. The filtrate is evaporated to dryness, leaving a brown oil. The oil is dissolved in 200 ml of methyl alcohol and 100 ml of 3N hydrochloric acid and this solution is stirred at ambient temperature for 18 hours and then basified with 6 N sodium hydroxide. The alkaline mixture is extracted with ethyl acetate and the ethyl acetate extracts are successively dried and evaporated to dryness, leaving an oil. The oil is chromatographed on a silica gel column eluting with chloroform which leads to a solid. The solid is dissolved in ether where it is converted to its hydrochloric acid salt, a white precipitate. The precipitate is recrystallized twice from ethyl alcohol to give the product 2,3-dihydro-1'-[3-(4-fluorobenzoyl)propyl]-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride, mp 245°-247° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated to dryness
  3. customleaving a brown oil
  4. extractionThe alkaline mixture is extracted with ethyl acetate
  5. dry with materialthe ethyl acetate extracts are successively dried
  6. customevaporated to dryness
  7. customleaving an oil
  8. customThe oil is chromatographed on a silica gel column
  9. washeluting with chloroform which
  10. dissolutionThe solid is dissolved in ether where it
  11. customThe precipitate is recrystallized twice from ethyl alcohol

Sources & evidence

ORD record
ord-ce11ef7c553840ae9c20a303cba8dce1
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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