Sodium Methoxide → HCID 57525458, compound

HRID 2241776Notes

Reaction equation

HRID 2241776 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:3]=1.[CH3:21][O-:22].[Na+]>CO>[CH3:21][O:22][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57525457HCID 57525457, compound

Product 1

HCID 57525458HCID 57525458, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-chloro-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-nicotinonitrile (Example 115) in methanol (0.2 M) was treated with sodium methoxide (4 equiv) at reflux temperature for 4 h. The mixture was cooled to rt, diluted with satd. aq. NaHCO3, and extracted with chloroform. The organic extract was dried (Na2SO4), filtered, and concentrated to yield 4-methoxy-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-nicotinonitrile (100%). This intermediate was converted to the title compound according to Example 115. MS (electrospray): mass calculated for C23H30ClN4O2, 394.24; m/z found, 395.4 [M+H]+.

Workup

  1. temperatureat reflux temperature for 4 h
  2. additiondiluted with satd
  3. extractionaq. NaHCO3, and extracted with chloroform
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ea73bd9136c4ea5bde90ce7bbff561a
Source dataset
uspto-grants-2010_05
Patent number
US07723527B2

Reaction notes

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