Diisopropylethylamine → HCID 59565074, compound

HRID 1895906Notes

Reaction equation

HRID 1895906 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl.O.[NH:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:18]2[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 2723901Piperonylamine

Product 1

HCID 59565074HCID 59565074, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Trifluoromethoxyphenylsulfonyl chloride (4.34 g, 16.7 mmol) was added to a solution of 4-piperidone monohydrate hydrochloride (2.99 g, 19.5 mmol) and N,N-diisopropylethylamine (9.50 ml, 57.5 mmol) in CH2Cl2 (50 ml) at 0° C. and stirred at room temperature for 20 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (250 ml), washed with aqueous 1 N HCl solution (50 ml), H2O (50 ml), saturated aqueous NaHCO3 solution (50 ml) and brine (50 ml), dried over Na2SO4 and concentrated in vacuo to give 1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-one (4.37 g, 81%) as a off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate (250 ml)
  3. washwashed with aqueous 1 N HCl solution (50 ml), H2O (50 ml), saturated aqueous NaHCO3 solution (50 ml) and brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5c7551a34a8491b81f01cbc7cc00dde
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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