Sodium hydride → HCID 20399406, compound

HRID 1981355Notes

Reaction equation

HRID 1981355 reaction equation
[CH3:1][C:2]1[N:3]([CH2:8][CH2:9][CH2:10][OH:11])[C:4]([CH3:7])=[CH:5][CH:6]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[CH:18]=[CH:17][N:16]=1>COCCOC>[CH3:1][C:2]1[N:3]([CH2:8][CH2:9][CH2:10][O:11][C:17]2[CH:18]=[C:19]([C:21]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:20]=[CH:15][N:16]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1289411854609-15-3HCID 18771703(2-Chloropyridin-4-yl)(piperidin-1-yl)methanone

Product 1

HCID 20399406HCID 20399406, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 0.047 mol of 2.5-dimethyl-1-(3-hydroxypropyl)pyrrole and 0.059 mol of 80% sodium hydride in 150 ml of 1,2-dimethoxyethane, previously heated at reflux for 15 minutes and cooled, is added 0.044 mol of 2-chloro-4-piperidino carbonylpyridine, then the reaction mixture is heated two hours with reflux and evaporated to dryness. The residue is taken up with water and extracted with ethyl acetate. The organic phase is separated and evaporated to dryness. Thus, 15.4 g of an oily product are obtained.

Workup

  1. temperaturepreviously heated
  2. temperatureat reflux for 15 minutes
  3. temperaturecooled
  4. temperaturethe reaction mixture is heated two hours
  5. temperaturewith reflux
  6. customevaporated to dryness
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is separated
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-fff140c4919a4331b0708ce900434650
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

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