Hydrochloric Acid → 1-[(4-n-Butoxyphenyl)sulfonyl]pipecolinic acid

HRID 1954083Notes

Reaction equation

HRID 1954083 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20].Cl>O.O1CCOCC1.CN(C)C1C=CN=CC=1>[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:1]2[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]2[C:3]([OH:5])=[O:4])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 849Pipecolic AcidHCID 8471TriethylamineHCID 5179904-Butoxybenzenesulfonyl Chloride

Product 1

HCID 232960261-[(4-n-Butoxyphenyl)sulfonyl]pipecolinic acid

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Pipecolinic acid (0.331 g, 2.56 mmol) is dissolved in 16 mL mixture of water and p-dioxane (1:1) followed by the addition of triethyl amine (0.78 mL, 5.64 mmol), 4-butoxyphenylsulfonyl chloride (0.67 g, 2.69 mmol), and 4-dimethylaminopyridine (0.031 g, 0.25 mmol). The resulting solution is stirred at room temperature overnight. The reaction mixture is acidified with 1N HCl and extracted three times with ethyl acetate. The combined organic extracts are washed with ammonium chloride, dried (MgSO4), filtered and evaporated to give the crude compound. Cl+ MS: m/z (rel intensity) 342 (M+ +H, 100).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts are washed with ammonium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-39dcfa2c32864166874a39abdfab1930
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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