Diisopropylethylamine → 1-(3-Methanesulfonyl-benzoyl)-piperidin-4-one

HRID 1060818Notes

Reaction equation

HRID 1060818 reaction equation
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:25][S:26]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([OH:34])=O)(=[O:28])=[O:27].Cl.[NH:39]1[CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>ClCCl>[CH3:25][S:26]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([N:39]1[CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40]1)=[O:34])(=[O:27])=[O:28]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2203803-Methanesulfonylbenzoic acidHCID 2733179PyBroPHCID 30848514-Piperidone hydrochloride

Product 1

HCID 223974901-(3-Methanesulfonyl-benzoyl)-piperidin-4-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBrOP™ (17.3 g) was added to a stirred mixture of 3-methanesulphonyl benzoic acid (7.35 g), 4-piperidone hydrochloride (5 g) and Hunig's base (25 ml) in dichloromethane (250 ml) with stirring at RT. The mixture was stirred overnight then washed with saturated NaHCO3 solution (200 ml) and then with saturated brine (200 ml). The organic layer was evaporated and the resulting residue purified by column chromatography (silica, 1:1 ethyl acetate: dichloromethane) to give the product as a thick oil (9.6 g; MS: APCI+(M+H) 282).

Workup

  1. stirringThe mixture was stirred overnight
  2. washthen washed with saturated NaHCO3 solution (200 ml)
  3. customThe organic layer was evaporated
  4. customthe resulting residue purified by column chromatography (silica, 1:1 ethyl acetate: dichloromethane)

Sources & evidence

ORD record
ord-8137ea8df40446309bdcc85617ebbd69
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Reaction notes

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