Methanesulfonyl chloride → 4-Benzoyl-1-methanesulphonylpiperidine

HRID 900757

Reaction equation

HRID 900757 reaction equation
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]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27244374-Benzoylpiperidine hydrochloride

Product 1

HCID 160435364-Benzoyl-1-methanesulphonylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-aa78a692c2cb4f939b8c603d3c78b629
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Linked notes

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