Triethylamine → HCID 18918530, compound

HRID 1291885Notes

Reaction equation

HRID 1291885 reaction equation
C(N(CC)CC)C.Cl.Cl.Cl.[N:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[CH2:33]([S:37](Cl)(=[O:39])=[O:38])[CH2:34][CH2:35][CH3:36]>ClCCl>[N:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([CH2:29][NH:30][S:37]([CH2:33][CH2:34][CH2:35][CH3:36])(=[O:39])=[O:38])=[CH:31][CH:32]=3)[CH2:19][CH2:18]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 131719608HCID 131719608, compound

Product 1

HCID 18918530HCID 18918530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.41 ml) was added to a stirred suspension of 4-[2-[4-(4-pyridyl)piperazin-1-yl]ethyl]benzylamine, trihydrochloride (300 mg) in dry dichloromethane (20 ml). After 5 minutes, 1-butanesulphonyl chloride (0.10 ml) was added and the mixture stirred overnight. Dichloromethane (80 ml) was added and the solution washed with water (2×25 ml), dried (MgSO4) and the solvent removed in vacuo. Trituration of the residue with a small volume of ethyl acetate gave the title compound, 50 mg, as an off-white solid: m.p. 154°-156° C.; NMR (d6DMSO) δ 8.16 (2H, d), 7.53 (1H, t), 7.22 (4H, m), 6.37 (2H, d), 4.10 (2H, d), 3.35 (6H, m+H2O), 2.81 (4H, m), 2.54 (4H, m+DMSO), 1.56 (2H, m), 1.29 (2H, m), 0.82 (3H, t); m/e 417 (M+H)+ ; calculated for C22H32N4O2 S.0.75H2O: C, 61.5; H, 7.8; N, 13.0. found: C, 61.5, H, 7.6; N, 12.7%.

Workup

  1. washthe solution washed with water (2×25 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-35af41ea162144c4b43d8e1f0476162b
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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