Hydrochloric Acid → HCID 66956465, compound

HRID 1042056Notes

Reaction equation

HRID 1042056 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:27])[CH2:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[CH3:26])[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl.C(OC(=O)C)C>C1COCC1>[CH3:26][C:20]1[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=1[CH2:18][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH2:12][CH2:13]1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 669564672-{1-[2-(2,5-Dimethyl-phenyl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 66956465HCID 66956465, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{1-[2-(2,5-dimethyl-phenyl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester (10.46 g, 27.06 mmol) in THF (30 mL) is added aqueous solution of sodium hydroxide (2 M, 20.3 mL) at RT. After stirring 3 h at RT, the reaction mixture is acidified with aqueous solution of HCl (2 M) until pH 2-3, and ethylacetate (30 mL) is added to the reaction mixture, and layers are separated. The aqueous layer is extracted with ethyl acetate (20 mL) and the combined organic layers are washed with brine (10 mL), dried over sodium sulafte, filtered, and evaporated under reduced pressure to give 2-{1-[2-(2,5-dimethyl-phenyl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid (5.9 g, 60.8%), which can be used in the next step without further purification. 1H-NMR (400 MHz, d6-DMSO): δ=1.55-1.65 (m, 2H), 2.01-2.12 (m, 2H), 2.15 (s, 3H), 2.22 (s, 3H), 2.77-2.86 (m, 1H), 3.18-3.29 (m, 1H), 3.65 (d, 2H), 3.98-4.07 (m, 1H), 4.45-4.53 (m, 1H), 6.90 (s, 1H), 6.92 (s, 1H), 6.93 (s, 1H), 7.04 (d, 1H), 8.49 (br, 1H), 12.95 (s, 1H). MS: m/z=359 (M+1).

Workup

  1. additionis added to the reaction mixture, and layers
  2. customare separated
  3. extractionThe aqueous layer is extracted with ethyl acetate (20 mL)
  4. washthe combined organic layers are washed with brine (10 mL)
  5. dry with materialdried over sodium sulafte
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ddbcfe7b30c94f71aca724eb9195ee53
Source dataset
uspto-grants-2013_10
Patent number
US08557821B2

Reaction notes

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