Triethylamine → HCID 60675749, compound

HRID 2245539Notes

Reaction equation

HRID 2245539 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[Cl:19][C:20]1[N:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[Cl:19][C:20]1[N:25]=[CH:24][C:23]([S:26]([N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:2]([CH3:11])[CH3:1])[CH2:6][CH2:7]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 60675749HCID 60675749, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dimethyl-N-(2-piperazin-1-ylethyl)amine (0.80 g, 5.0 mmol) and triethylamine (1.0 g, 10 mmol) in dichloromethane (7 mL) was added 6-chloropyridine-3-sulfonyl chloride (1.0 g, 5.0 mmol; described in: Naegeli et al. Helv. Chim. Acta, 1938, 21, 1746, 1750) in dichloromethane (3 mL) at room temperature. After stirring over night at room temperature the solvent was removed in vacuo, the residue was partitioned between aqueous sodium hydroxide (2 M), diethyl ether (3×15 mL), and dichloromethane (3×15 mL). The combined extracts were dried (MgSO4), and the solvents were removed in vacuo to afford 1.3 g of the crude product. The residue was purified on a silica gel column using acetonitrile/triethylamine, (90:10), as the eluent to afford 1.0 g (60% yield) of title compound: 1H NMR (CDCl3, 400 MHz) δ 8.73 (d, J=2 Hz, 1H), 7.95 (dd, J=8, 2 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 3.08 (t, J=5 Hz, 4H), 2.56 (t, J=5 Hz, 4H), 2.47 (t, J=7 Hz, 2H), 2.35 (t, J=7 Hz, 2H), 2.19 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 155.8, 148.8, 137.8, 131.3, 124.6, 56.7, 56.0, 52.4, 45.8, 45.8.

Workup

  1. customwas removed in vacuo
  2. customthe residue was partitioned between aqueous sodium hydroxide (2 M), diethyl ether (3×15 mL), and dichloromethane (3×15 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvents were removed in vacuo
  5. customto afford 1.3 g of the crude product
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-9e65ec10919d4013bb83f6a9ef9a9605
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

Loading…