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

HRID 2259930Notes

Reaction equation

HRID 2259930 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(Cl)Cl>[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 257103Ethyl 1-(phenylsulfonyl)piperidine-4-carboxylateYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl isonipecotate (15.7 g, 0.1 mol) in methylene chloride (100 mL) at 0° C. was treated with pyridine (10 mL) and then benzenesulfonyl chloride (17.6 g, 0.1 mol). The reaction was warmed to room temperature and stirred at room temperature for 2 hours. The reaction was then poured into 1 N HCl (1 L) and extracted with ethyl acetate (2×500 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The solid was recrystallized from ethyl acetate to give 17 g of product.

Workup

  1. extractionextracted with ethyl acetate (2×500 mL)
  2. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a7f5bcd758004ebeb5054a040c9ac7f1
Source dataset
uspto-grants-1995_12
Patent number
US05475109

Reaction notes

Loading…