Hydrochloric Acid → Ethyl 1-(phenylsulfonyl)piperidine-4-carboxylate

HRID 2104430Notes

Reaction equation

HRID 2104430 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH3:2].C(N(CC)CC)C.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][CH2:7][N:8]([S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])[CH2:9][CH2:10]1)=[O:11])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 257103Ethyl 1-(phenylsulfonyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To isonipecotic acid ethyl ester (1.08 mL) dissolved in tetrahydrofuran (10 mL), triethylamine (1.40 mL) was added, and benzenesulfonyl chloride (1.02 mL) was added thereto at 0° C. The resultant mixture was stirred at room temerature for 21 hours. Ice was added to the mixture, followed by stirring for 10 minutes. Ethyl acetate and 0.5N hydrochloric acid were added thereto to thereby give two layers. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride. The resultant mixture was dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1), to thereby give the title compound (1.66 g) as a white solid.

Workup

  1. customat 0° C
  2. additionIce was added to the mixture
  3. customto thereby give two layers
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  5. dry with materialThe resultant mixture was dried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-71d3a01a91e04310aed0cab51e25e548
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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