HCID 12694049, compound → HCID 12694077, compound

HRID 647528Notes

Reaction equation

HRID 647528 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][S:7][C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3F)[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CS(C)=O.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]2[S:7][C:8]3([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 12694049HCID 12694049, compound

Product 1

HCID 12694077HCID 12694077, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of sodium methylsulfinylmethide is produced from 0.7 g of (50%) sodium hydride and 15 ml of dimethylsulfoxide as in Example 1c. A solution of 4.2 g of 4-(4-chlorobenzylthio)-4-(2-fluorophenyl)-1-methylpiperidine, free base of a, in 15 ml of dimethylsulfoxide is added to this solution over a three minute span. After total addition, the mixture is stirred at ambient temperature for one hour and then poured onto 70 ml of ice-water. The mixture is diluted with water to 120 ml total volume before being filtered to collect the crude product. The product is washed with water and then dissolved with ether. The ethereal solution is sequentially washed thrice with water and once with a saturated sodium chloride solution and dried to give yellow-white crystals. The crystals are chromatographed with ether through an alumina column to give white crystals, mp 121°-123° C. of 3-(4-chlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine].

Workup

  1. additionAfter total addition
  2. filtrationbefore being filtered
  3. customto collect the crude product
  4. washThe product is washed with water
  5. dissolutiondissolved with ether
  6. dry with materialonce with a saturated sodium chloride solution and dried
  7. customto give yellow-white crystals
  8. customThe crystals are chromatographed with ether through an alumina column

Sources & evidence

ORD record
ord-d14b5dc891b34bbdac3fdccc6e526fe1
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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