Hydrochloric Acid → Methyl 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid Methyl Ester

HRID 2059893Notes

Reaction equation

HRID 2059893 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([S:32](Cl)(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=1.Cl>ClCCl>[CH3:2][O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:32]([C:28]1[C:29]([CH3:31])=[CH:30][C:25]([O:24][CH3:23])=[CH:26][C:27]=1[CH3:36])(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 67316706Methyl 4-(piperidin-2-yl)butanoic acid methyl ester hydrochloride

Product 1

HCID 67316484Methyl 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 4-(piperidin-2-yl)butanoic acid methyl ester hydrochloride (1.26 g, 5.683 mmol) was dissolved in dichloromethane (25 ml) and triethylamine (4 ml, 28.417 mmol) and a solution of 4-methoxy-2,6-dimethylbenzenesulfonic acid chloride (2.67 g, 11.37 mmol) in dichloromethane (10 ml) was added. The mixture was stirred overnight at room temperature. 1 mol/l HCl solution (10 ml) was added to the reaction mixture, followed by phase separation and extraction of the aqueous phase with dichloromethane (2×20 ml). The combined organic phases were washed with saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated to small volume under vacuum. The crude product was purified by column chromatography (silica gel) with hexane/dichloromethane/diethyl ether (400:100:50). Yield: 1.65 g (75%)

Workup

  1. customfollowed by phase separation and extraction of the aqueous phase with dichloromethane (2×20 ml)
  2. washThe combined organic phases were washed with saturated sodium chloride solution (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to small volume under vacuum
  5. customThe crude product was purified by column chromatography (silica gel) with hexane/dichloromethane/diethyl ether (400:100:50)

Sources & evidence

ORD record
ord-067172eae71743e78297fc6858b62e6b
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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