Sodium Hydroxide → 1-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid

HRID 907536Notes

Reaction equation

HRID 907536 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:16]([Cl:17])=[N:15][S:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CCO>[Cl:17][C:16]1[C:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[N:13][S:14][N:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 590139411-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 590139601-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid ethyl ester (12.3 g, 45 mmol) was dissolved in EtOH (70 mL) to which was added 5N NaOH (15 mL). The mixture was stirred at room temperature for 2 h, then concentrated in vacuo. The resulting aqueous solution was further diluted with H2O, washed with EtOAc (3×) and acidified to pH 2.0 with conc'd HCl. The resulting precipitate was filtered, washed with H2O and dried under high vacuum to give 8.44 g (77%) of 1-(4-chloro-[1,2,5]thiadiazol-3-yl)-piperidine-4-carboxylic acid. 1H NMR (CDCl3) 3.97-3.92 (m, 2H), 3.03 (m, 2H), 2.59 (m, 1H), 2.06 (m, 2H), 1.93 (m, 2H) ppm. LC-MS (M−)=246.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resulting aqueous solution was further diluted with H2O
  3. washwashed with EtOAc (3×)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with H2O
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-b3e036f8c59844889abbde2306d6e80b
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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