Hydrochloric Acid → HCID 66955907, compound

HRID 1042058Notes

Reaction equation

HRID 1042058 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]=[C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:29])[CH2:20][C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[CH3:28])[CH2:15][CH2:14]2)[S:11][CH:12]=1)(C)(C)C.[ClH:31]>O1CCOCC1>[ClH:31].[NH2:7][C:8]1[N:9]=[C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:29])[CH2:20][C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=3[CH3:28])[CH2:15][CH2:14]2)[S:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66957001(2-{1-[2-(2,5-Dimethyl-phenyl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-carbamic acid tert-butyl ester

Product 1

HCID 66955907HCID 66955907, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2-{1-[2-(2,5-dimethyl-phenyl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-carbamic acid tert-butyl ester (5.65 g, 13.15 mmol) is added a solution of 4M HCl in dioxane (35 mL) at RT. After stirring 3 days at RT, the solvent is evaporated under reduce pressure. The resulting solid is triturated with diethylether, and filtered to give 1-[4-(4-amino-thiazol-2-yl)piperidin-1-yl]-2-(2,5-dimethyl-phenyl)-ethanone hydrochloride salt, which is suspended in aqueous saturated sodium bicarbonate (500 mL). After stirring 30 min at RT, the reaction mixture is extracted with ethyl acetate (500 mL). The combined organic layers are washed with water (100 mL) and brine (100 mL), filtered, dried over sodium sulfate, and evaporated under reduced pressure to give 1-[4-(4-amino-thiazol-2-yl)-piperidin-1-yl]-2-(2,5-dimethyl-phenyl)-ethanone (3.27 g, 75%). 1H-NMR (400 MHz, CDCl3): δ=1.53-1.61 (m, 1H), 1.67-1.79 (m, 1H), 1.95-2.04 (m, 1H), 2.08-2.13 (m, 1H), 2.25 (s, 3H), 2.30 (s, 3H), 2.78-2.88 (m, 1H), 3.06-3.20 (m, 2H), 3.68 (s, 2H), 3.80-3.89 (m, 1H), 4.05 (s, 1H), 4.68-4.74 (m, 1H), 6.95 (s, 1H), 6.98 (d, 1H), 7.07 (d, 1H), 7.23 (s, 1H). MS: m/z=330 (M+1). MS: m/z=330 (M+1).

Workup

  1. customthe solvent is evaporated
  2. customThe resulting solid is triturated with diethylether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ddd636dbf84c40e4858c8bb8b5272c69
Source dataset
uspto-grants-2013_10
Patent number
US08557821B2

Reaction notes

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