Potassium Hydroxide → HCID 58423310, compound

HRID 1398025Notes

Reaction equation

HRID 1398025 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[O:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH:12]([NH:17]C(=O)OC)[CH2:11]1.[OH-].[K+]>CO.O>[NH2:17][CH:12]1[CH:13]([CH3:16])[CH2:14][CH2:15][N:10]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH:8]=[O:9])[CH2:11]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58423179HCID 58423179, compound

Product 1

HCID 58423310HCID 58423310, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 1-(2-chloro-6-formylphenyl)-4-methylpiperidin-3-ylcarbamate (220 mg, 0.71 mmol) (Method 119) in MeOH (3 ml) was added 40% aqueous solution of KOH (10 ml) drop wise, and the resulting mixture was heated at reflux for 16 h. The mixture was allowed to cool to rt, diluted with water, and extracted with DCM. The combined organic extract was dried over anhydrous Na2SO4, filtered, and conc. in vacuo. The resulting residue was purified via silica gel chromatography (100% ethyl acetate to 10% methanol in ethyl acetate) to yield the title compound as a light yellow gum (0.057 g, 31.9%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.44 (s, 1 H), 7.40 (t, 2 H), 7.07 (t, 1 H), 4.29 (d, 1 H), 3.58 (ddd, 1 H), 3.38 (dd, 1 H), 3.11 (td, 1 H), 2.81 (d, 1 H), 2.20-1.91 (m, 1 H), 1.31-1.14 (m, 1 H), 1.08 (d, 3 H), 0.63-0.37 (m, 1 H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with DCM
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe resulting residue was purified via silica gel chromatography (100% ethyl acetate to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-ee98350884164ea5b83e96bfcf11e670
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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