Potassium Iodide → HCID 13253839, compound

HRID 647533Notes

Reaction equation

HRID 647533 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:21][C:15]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)=[CH:4][CH:3]=1.Cl[CH2:23][CH:24]1[CH2:26][CH2:25]1.[I-].[K+].C(=O)(O)[O-].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38]>CN(C)C=O.O.C(Cl)Cl>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:21][C:15]3([CH2:16][CH2:17][N:18]([CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH2:19][CH2:20]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 80013(Chloromethyl)cyclopropaneHCID 444266Maleic AcidHCID 516892Sodium BicarbonateHCID 12694115HCID 12694115, compound

Product 1

HCID 13253839HCID 13253839, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.0 g of 3-(4-chlorophenyl)-1,3-dihydrospiro[benzo(c)thiophene-1,4'-piperidine], Example 15, 0.7 g of chloromethylcyclopropane, 1.4 g of potassium iodide and 1.4 g of sodium bicarbonate in 20 ml of dimethylformamide is heated with stirring at 80°-85° C. for 17 hours. The reaction mixture is permitted to cool to ambient temperature before being diluted with 75 ml of water and 30 ml of methylene chloride. The aqueous phase is extracted twice with methylene chloride and all the methylene chloride solutions are combined. The combined solutions are washed, sequentially, with water and saturated sodium chloride solution and then dried effecting a clear oil. The oil is chromatographed on an alumina column with an ether eluant to obtain the oil with enhanced purity. This oil is converted to its maleic acid salt which is recrystallized from an acetone-ether mixture to obtain the salt, mp 217.5°-218° C. of 3-(4-chlorophenyl)-1'-cyclopropylmethyl-1,3-dihydrospiro[benzo(c)thiophene-1,4'-piperidine] maleate.

Workup

  1. temperatureis heated
  2. extractionThe aqueous phase is extracted twice with methylene chloride and all the methylene chloride solutions
  3. washThe combined solutions are washed
  4. dry with materialsequentially, with water and saturated sodium chloride solution and then dried
  5. customThe oil is chromatographed on an alumina column with an ether eluant
  6. customto obtain the oil with enhanced purity
  7. customis recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-8dc72706bfe94d99859124bab3cc9a9c
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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