Triethylamine → N-{4-[2-(4-[4-pyridinyl]-1-piperazinyl)ethyl]phenyl}methanesulphonamide

HRID 1382221Notes

Reaction equation

HRID 1382221 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.CS(O[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][CH:21]=1)(=O)=O.C(N(CC)CC)C>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:24][CH:25]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 149859624-Methanesulphonamidophenethyl mesylate

Product 1

HCID 21274454N-{4-[2-(4-[4-pyridinyl]-1-piperazinyl)ethyl]phenyl}methanesulphonamideYield 20.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-pyridinyl)piperazine (1.63 g), N-[4-(2-methylsulphonyloxyethyl)phenyl]methanesulphonamide (2.93 g) and triethylamine (1.01 g) in ethanol (25 ml) was heated under reflux for 18 hours and then evaporated. The resulting oil was partitioned between dichloromethane and water (some insoluble material remained in the aqueous layer). The aqueous layer was washed with dichloromethane and the organic layers were combined, washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed in silica gel. Elution with dichloromethane/methanol (19:1) first gave some impurity followed by a solid which was crystallised from methanol/ethyl acetate to give the title compound (0.75 g), m.p. 208°-210° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. customevaporated
  3. customThe resulting oil was partitioned between dichloromethane and water (some insoluble material
  4. washThe aqueous layer was washed with dichloromethane
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customwas chromatographed in silica gel
  10. washElution with dichloromethane/methanol (19:1)
  11. customfirst gave some impurity
  12. customwas crystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-04f1c317b8b5447b913ac5750b216c7c
Source dataset
uspto-grants-1989_02
Patent number
US04806536

Reaction notes

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