Tetrahydrofuran → 4-(2,4-Dichlorophenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile

HRID 1164356Notes

Reaction equation

HRID 1164356 reaction equation
[OH-].[Na+].Cl[CH2:4][CH2:5][N:6]([CH2:17][CH2:18]Cl)[S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][C:29]#[N:30].O1CCCC1>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O.CC1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[C:28]1([C:29]#[N:30])[CH2:4][CH2:5][N:6]([S:7]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)(=[O:8])=[O:9])[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 805662,4-DichlorophenylacetonitrileHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamide

Product 1

HCID 130942454-(2,4-Dichlorophenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrileYield 29%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred and hot solution of 8.5 parts of N,N,N-triethylbenzenemethanaminium chloride, 40 parts of sodium hydroxide and 360 parts of a sodium hydroxide solution 50%, is added dropwise a solution of 72.7 parts of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide and 45.5 parts of 2,4-dichlorobenzeneacetonitrile in 90 parts of tetrahydrofuran. Upon completion, stirring is continued for 3 hours at 50° C. The reacton mixture is cooled, 216 parts of methylbenzene and 480 parts of water are added and the layers are separated. The organic phase is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 28 parts (29%) of 4-(2,4-dichlorophenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile; mp. 145° C.

Workup

  1. stirringUpon completion, stirring
  2. temperatureThe reacton mixture is cooled
  3. customthe layers are separated
  4. washThe organic phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-eb059f2b7e88415b847055ea6f7afd51
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

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