Sodium Carbonate → 1-[5-Benzoyl-3-(pyridin-4-yl)thiophen-2-yl]piperidin-4-one

HRID 1869180Notes

Reaction equation

HRID 1869180 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[S:15][C:14]([C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:17])=[CH:13][C:12]=3[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.CC(C)=O>[C:16]([C:14]1[S:15][C:11]([N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[C:12]([C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH:13]=1)(=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 16093274HCID 16093274, compound

Product 1

HCID 160932771-[5-Benzoyl-3-(pyridin-4-yl)thiophen-2-yl]piperidin-4-oneYield 63%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of [5-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-4-pyridin-4-yl-thiophen-2-yl]-phenyl-methanone (39.5 mg, 0.097 mmole), p-toluenesulfonic acid monohydrate (37 mg, 0.194 mmole, 2 eq.), acetone (2 mL), and water (1 mL) was heated to reflux overnight. The solution was diluted with water and made basic to pH 14 with 4N sodium hydroxide or 1 M sodium carbonate solution. The solution was extracted twice with ethyl acetate. The organic extracts were dried over magnesium sulfate, filtered, and purified by column chromatography to provide the product as yellow solid (22 mg, 63%). 1H NMR (CDCl3) δ 8.61 (m, 2H), 7.81-7.45 (m, 8H), 3.46 (m, 4H), 2.52 (m, 4H). MS (m/z): 363 (MH+), 385 (MNa+).

Workup

  1. temperatureto reflux overnight
  2. extractionThe solution was extracted twice with ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-24f2e851f40843e5ab57ed9a6913b2c5
Source dataset
uspto-grants-2009_12
Patent number
US07638525B2

Reaction notes

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