Pyridine → HCID 70238278, compound

HRID 427433Notes

Reaction equation

HRID 427433 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#N.[NH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.[N:33]1C=CC=C[CH:34]=1>>[N:30]1[CH:31]=[CH:32][C:27]([N:24]2[CH2:23][CH2:22][N:21]([C:18]3[CH:17]=[CH:16][C:15]([C:14]#[N:13])=[CH:20][C:19]=3[CH2:34][NH:33][S:9]([C:6]3[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=3)(=[O:10])=[O:11])[CH2:26][CH2:25]2)=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 18357039HCID 18357039, compound

Product 1

HCID 70238278HCID 70238278, compound

Procedure

4-Cyanophenylsulphonyl chloride (202 mg) was added to a solution of 1-(4-aminomethylphenyl)-4-(4-pyridyl)piperazine (268 mg) in pyridine (20 ml). The mixture was heated on a steam bath for three hours. The solvents were removed by evaporation and water (100 ml) added to give a precipitate which was extracted into ethyl acetate (2×100 ml). The ethyl acetate extracts were combined, washed with water, brine, dried (MgSO4)-10% methanol/methylene chloride as eluent to give a solid which was recrystallised from a mixture of tetrahydrofuran/methanol/isohexane to give 1-(4-pyridyl)-4-(4-cyanophenylsulphonamidomethyl-phenyl)piperazine (52 mg) as a solid m.p.229-230° C.; microanalysis found: C,62.8; H,5.6; N,15.7%; C23H23N5O2S.0.25H2O requires: C,62.4; H,5.4; N,15.8%; NMR: 3.15-3.3(m,4H), 3.4-3.55(m,4H), 3.85-4.0(d,2H), 6.8-6.9(dd,4H), 7.0-77.1(d,2H), 7.8-7.9(d,2H), 7.95-8.05(d,2H), 8.18-8.25(d,2H), 8.25-8.4(bt,1H); MS: m/z 434 (MH)+

Workup

  1. temperatureThe mixture was heated on a steam bath for three hours
  2. customThe solvents were removed by evaporation and water (100 ml)
  3. additionadded
  4. customto give a precipitate which
  5. extractionwas extracted into ethyl acetate (2×100 ml)
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)-10% methanol/methylene chloride as eluent
  8. customto give a solid which
  9. customwas recrystallised from a mixture of tetrahydrofuran/methanol/isohexane

Sources & evidence

ORD record
ord-fd4abfc96001400cb34d68d4c7e061ec
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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