Acetyl chloride → HCID 86721885, compound

HRID 1049037Notes

Reaction equation

HRID 1049037 reaction equation
[CH2:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3].CCN(CC)CC.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:11]=[CH:10][C:9]([S:6]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])(=[O:8])=[O:7])=[CH:14][CH:13]=2)[CH2:16][CH2:17]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 28917028HCID 28917028, compound

Product 1

HCID 86721885HCID 86721885, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-isobutyl-4-piperazin-1-yl-benzenesulfonamide (1.14 g, 3.83 mmol) and Et3N (795 μL, 5.75 mmol) in DCM (25 mL) was treated with acetyl chloride (340 mL, 4.79 mmol) and stirred at room temperature for 30 minutes. The mixture was diluted with DCM, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (60-75% EtOAc in DCM) gave 4-(4-acetyl-piperazin-1-yl)-N-isobutyl-benzenesulfonamide (1.23 g, 95%) as a white solid. 1H NMR (400 MHz, DMSO) δ 7.58 (d, J=8.8 Hz, 2H), 7.27 (t, J=6.2 Hz, 1H), 7.04 (d, J=8.8 Hz, 2H), 3.62-3.54 (m, 4H), 3.38-3.26 (m, 8H), 2.49-2.43 (m, 2H), 2.04 (s, 3H), 1.65-1.54 (m, 1H), 0.80 (d, J=6.7 Hz, 6H). LCMS (m/z, Method B) ES+ 340.0 [M+1]+.

Workup

  1. washwashed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel column chromatography (60-75% EtOAc in DCM)

Sources & evidence

ORD record
ord-d833a1a77e474fa3a337722496de1c31
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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