Hydrochloric Acid → HCID 67225432, compound

HRID 2367882Notes

Reaction equation

HRID 2367882 reaction equation
CO[C:3]([C:5]1([NH:14][C:15](=[O:26])[CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH2:10][CH2:9][N:8]([N:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1)=[O:4].CC(C)([O-])C.[K+].O.Cl>CN(C)C=O>[CH3:13][N:11]([CH3:12])[N:8]1[CH2:7][CH2:6][C:5]2([NH:14][C:15](=[O:26])[CH:16]([C:17]3[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=3[CH3:23])[C:3]2=[O:4])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 67225581HCID 67225581, compound

Product 1

HCID 67225432HCID 67225432, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg 1-Dimethylamino-4-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-piperidine-4-carboxylic acid methyl ester (from Step 3) is dissolved in 5 ml N,N-dimethylformamide, and 466 mg potassium t-butoxide is added. The mixture is stirred at room temperature for 18 hours. Then water is added, and the pH adjusted to 5.2 by the addition of aqueous hydrochloric acid. The mixture is extracted with ethyl acetate, the organic layer washed with brine, dried over sodium sulfate, and the solvent evaporated. The residue is purified by chromatography on silica gel, with toluene/ethanol/dioxane/triethylamine/water (20:8:4:4:1) as a solvent. Thus, 196 mg 8-Dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione is obtained as a solid, mp 237-241° C. 1H-NMR (d4-methanol): 6.94 ppm (s, 2H), 3.09 ppm (m, 2H), 2.79 ppm (m, 2H), 2.53 ppm (s, 6H), 2.28 ppm (m, 5H), 2.16 ppm (s, 6H), 1.64 ppm (m, 2H).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe organic layer washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent evaporated
  5. customThe residue is purified by chromatography on silica gel, with toluene/ethanol/dioxane/triethylamine/water (20:8:4:4:1) as a solvent

Sources & evidence

ORD record
ord-8dbdc0ce456f4594aa0b4b8e2d56ddae
Source dataset
uspto-grants-2014_04
Patent number
US08703165B2

Reaction notes

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