Triethylamine → N-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenyl]-4-methylphenylsulphonamide

HRID 864773Notes

Reaction equation

HRID 864773 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.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1)=[O:16].C(N(CC)CC)C>C(O)(C)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:25])=[O:26])=[CH:21][CH:22]=3)=[O:16])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 16637184N-[4-(2-Bromoacetyl)phenyl]-4-methylbenzenesulfonamide

Product 1

HCID 18918408N-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenyl]-4-methylphenylsulphonamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(4-pyridyl)piperazine (1.79 g), N-(4-bromoacetylphenyl)-4-methylphenylsulphonamide (3.68 g) and triethylamine (1.39 ml) in isopropanol (50 ml) was stirred for 18 hours. The precipitated solid was collected, triturated with dichloromethane, filtered and dried. This solid was further purified by flash chromatography on neutral alumina eluting successively with dichloromethane, 2.5% v/v methanol/dichloromethane then 5% v/v methanol/dichloromethane. Evaporation of the desired fractions to a small volume followed by addition of dichloromethane gave a crystalline solid. This solid was collected, washed with dichloromethane to give the title compound, 440 mg, as crystals: m.p. 168°-170° C.; NMR (d6DMSO) δ8.14(2H,d), 7.86(2H,d), 7.71(2H,d), 7.35(2H,d), 7.18(2H,d), 6.80(2H,d), 3.79(2H,s), 3.31(4H,t), 2.59(4H t), 2.33(3H,s); m/e 451 (M+H)+ ; calculated for C24H26N4O3S: C, 64.0; H, 5.8; N, 12.4. found C, 63.4; H, 5.7; N, 12.2%.

Workup

  1. customThe precipitated solid was collected
  2. customtriturated with dichloromethane
  3. filtrationfiltered
  4. customdried
  5. customThis solid was further purified by flash chromatography on neutral alumina eluting successively with dichloromethane, 2.5% v/v methanol/dichloromethane
  6. customEvaporation of the desired fractions to a small volume
  7. additionfollowed by addition of dichloromethane
  8. customgave a crystalline solid
  9. customThis solid was collected
  10. washwashed with dichloromethane

Sources & evidence

ORD record
ord-bf105b281d134dcf83cfb11a9fb8723b
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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