Acetyl chloride → HCID 22500825, compound

HRID 398275Notes

Reaction equation

HRID 398275 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH2:6][C:7]1([NH:13][S:14]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(N(CC)CC)C.CCOC(C)=O.CCCCCC>C(Cl)Cl>[C:1]([N:10]1[CH2:9][CH2:8][C:7]([NH:13][S:14]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)(=[O:15])=[O:16])([CH2:6][OH:5])[CH2:12][CH2:11]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21226206Ethyl acetate hexaneHCID 22500834HCID 22500834, compound

Product 1

HCID 22500825HCID 22500825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
25 °C

Procedure

Acetyl chloride (0.15 g, 1.894 mmol) was added dropwise (5 min) as a solution in CH2Cl2 (1 mL) to a cold 0° C. solution of N-[4-(hydroxymethyl)piperidin-4-yl]-5-chloro-thiophene-2-sulfonamide (0.19 g, 0.61 mmol) in CH2Cl2 (5 mL) and triethylamine (0.44 mL, 3.18 mmol) The solution was allowed to warm to 25° C. overnight (19 h). An aliquot was taken and TLC (1:1 EtOAc-hexane) indicated that reaction was complete. It was diluted with CH2Cl2 (10 mL) and the organic layer was washed with 1N HCl (50 mL), saturated aqueous NaHCO3 (50 mL) and NaCl (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated to obtain a crude oil (175 mg). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluent: starting with 1:4 EtOAc-hexane and ending with 1:1 EtOAc-hexane to afford N-[1-Acetyl-4-(hydroxymethyl)-piperidin-4-yl]-5-chlorothiophene-2-sulfonamide as yellowish color oil (62 mg, 28.9%). Mass Spectrum (+ESI): 353 (M+H)+. Anal. Calc'd for C12H17ClN2O4S2.1.62H2O: C, 37.29; H, 5.70; N, 7.26. Found: C, 37.62; H, 5.36; N, 7.31.

Workup

  1. washthe organic layer was washed with 1N HCl (50 mL), saturated aqueous NaHCO3 (50 mL) and NaCl (50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain a crude oil (175 mg)
  6. customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluent

Sources & evidence

ORD record
ord-d358026fae7142fc8cc94a09fec59ac3
Source dataset
uspto-grants-2003_08
Patent number
US06610734B2

Reaction notes

Loading…