Methanesulfonyl chloride → 4-Benzoyl-1-methanesulphonylpiperidine

HRID 900757

Reaktionsgleichung

Reaktionsgleichung von HRID 900757
CCN(C(C)C)C(C)C.Cl.[C:11]1([C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([N:22]1[CH2:23][CH2:24][CH:19]([C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:18])[CH2:20][CH2:21]1)(=[O:28])=[O:27]

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27244374-Benzoylpiperidine hydrochloride

Produkt 1

HCID 160435364-Benzoyl-1-methanesulphonylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Neat DIPEA (1.54 ml, 8.86 mmol) was added dropwise to a solution of phenyl(4-piperidinyl)methanone hydrochloride (1 g, 4.43 mmol) in CH2Cl2 (20 ml) at 0° C. Then, neat MsCl (377 μL, 4.87 mmol) was slowly added and the cooling bath was removed. After 30 minutes, the reaction was quenched with water and diluted with CH2Cl2. After separation, the organic phase was washed with brine, dried over MgSO4 and evaporated to dryness. The final ketone 1 was obtained as a white solid (1.16 g, 98%).

Aufarbeitung

  1. customthe cooling bath was removed
  2. customthe reaction was quenched with water
  3. additiondiluted with CH2Cl2
  4. customAfter separation
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-aa78a692c2cb4f939b8c603d3c78b629
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361668B2

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