4-Toluenesulfonyl chloride → HCID 70239088, compound

HRID 427430Notes

Reaction equation

HRID 427430 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1.[CH2:32](N(CC)CC)C>ClCCl>[N:29]1[CH:30]=[CH:31][C:26]([N:23]2[CH2:22][CH2:21][N:20]([C:17]3[CH:16]=[CH:15][C:14]([CH2:13][NH:12][S:7]([C:4]4[C:5]([CH3:32])=[CH:6][CH:1]=[CH:2][CH:3]=4)(=[O:8])=[O:9])=[CH:19][CH:18]=3)[CH2:25][CH2:24]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18357039HCID 18357039, compound

Product 1

HCID 70239088HCID 70239088, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-toluenesulphonyl chloride (0.38 g) in dichloromethane (25 ml) was added dropwise to a stirred solution of 1-(4-aminomethylphenyl)-4-(4-pyridyl)piperazine (536 mg) in dichloromethane (50 ml) containing triethylamine (0.5 ml). The reaction mixture was stirred at ambient temperature overnight. The mixture was washed with aqueous sodium carbonate solution, water, brine, dried (MgSO4) and evaporated. The residue was recrystallised from methanol to give 1-(4-pyridyl)-4-(4-toluenesulphonamidomethylphenyl)piperazine (0.36 g) as a solid, m.p. 196-198° C.; microanalysis, found: C, 65.2; H,6.2; N,13.2%; C23H26N4O2S requires: C,65.4; H,6.2; N,13.3%; NMR: 2.37(s, 3H), 3.15-3.3(m, 4H), 3.4-3.55(m, 4H), 3.81-3.88(d, 2H), 6.8-6.93(dd, 4H), 7.03-7.15 (d, 2H), 7.32-7.4(d, 2H), 7.6-7.7(d, 2H), 7.8-7.95(t, 1H), 8.1-8.2(d, 2H); MS: m/z 423 (MH)+.

Workup

  1. washThe mixture was washed with aqueous sodium carbonate solution, water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-4e37d5b352d145999699e2051b154439
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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