Sodium Methoxide → HCID 57441145, compound

HRID 1517078Notes

Reaction equation

HRID 1517078 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.[CH3:32][O-:33].[Na+]>CO>[CH3:32][O:33][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 57441145HCID 57441145, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.55 g (1.2 mmol) of [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) in 10 ml of MeOH was treated with 2.25 ml (12.2 mmol) of a sodium methoxide solution (5.4 molar in MeOH) and the reaction mixture was heated up to reflux. After 18 hours, it was poured into crashed ice and extracted three times with CH2Cl2/2-propanol 4:1; the organic phases were dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1) to give 0.41 g (76%) of the title compound as light yellow oil. MS: 448.3 (MH+).

Workup

  1. temperaturethe reaction mixture was heated up
  2. temperatureto reflux
  3. additionit was poured
  4. extractionextracted three times with CH2Cl2/2-propanol 4:1
  5. dry with materialthe organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1)

Sources & evidence

ORD record
ord-528e167c8244435eb7e7d4f296ead43b
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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