Methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate → 1-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylic acid

HRID 1913164Notes

Reaction equation

HRID 1913164 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24]C)=[O:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1>Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([S:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 58494546Methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate

Product 1

HCID 584945551-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylic acidYield 44%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate (0.25 g, 0.69 mmol) in 5M aqueous HCl (2.5 mL) is heated at 80° C. for 18 h. The mixture is cooled to room temperature resulting in formation of a precipitate. The precipitate is filtered, washed sequentially with 5M aqueous HCl and MeCN and dried in air to give 0.10 g (44%) of 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylic acid. m/z=347 [M++H].

Workup

  1. customresulting in formation of a precipitate
  2. filtrationThe precipitate is filtered
  3. washwashed sequentially with 5M aqueous HCl and MeCN
  4. customdried in air

Sources & evidence

ORD record
ord-b02906d962724253b7f84066c68f2ff2
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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