Sodium amide → 4-(4-Chlorophenyl)-1-(p-tolylsulphonyl)piperidine-4-carbonitrile

HRID 616206Notes

Reaction equation

HRID 616206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][N:14]([CH2:25][CH2:26]Cl)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16].[NH2-].[Na+]>C1C=CC=CC=1>[C:21]1([CH3:24])[CH:20]=[CH:19][C:18]([S:15]([N:14]2[CH2:25][CH2:26][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([C:9]#[N:10])[CH2:12][CH2:13]2)(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 30163244-(4-Chlorophenyl)-1-(p-tolylsulphonyl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 60.3 parts of 4-chlorophenylacetonitrile and 118 parts of N,N-bis(2-chloroethyl)-4-toluenesulfonamide in 720 parts of dried benzene under N2 there is added portionwise with stirring at 10°-13° C 32.6 parts of sodamide. The cooling bath is then removed and the mixture is stirred for one hour during which time the temperature rises to 70° C and then falls back to 43° C. Ice cold water is added to the mixture and a fine solid forms. This is separated by filtration and washed successively with water and benzene and dried and then triturated in boiling methanol. The undissolved solid is separated by filtration, washed with water and dried to give 1-(4-toluenesulfonyl)-4-(4-chlorophenyl)-4-piperidinecarbonitrile melting at about 202°-206° C.

Workup

  1. customThe cooling bath is then removed
  2. customrises to 70° C
  3. customfalls back to 43° C
  4. additionIce cold water is added to the mixture
  5. customThis is separated by filtration
  6. washwashed successively with water and benzene
  7. customdried
  8. customtriturated
  9. customThe undissolved solid is separated by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-b64891f428ec44489031695f2cf7ddcd
Source dataset
uspto-grants-1978_02
Patent number
US04072686

Reaction notes

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