Water → HCID 15123334, compound

HRID 2111608Notes

Reaction equation

HRID 2111608 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1>[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)([OH:26])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 15123334HCID 15123334, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 22.2 g of 2-bromopyridine in 100 ml of THF is cooled to −70° C., 87.8 ml of n-butyllithium are added dropwise and the mixture is stirred for 30 minutes. A solution of 25.6 g of 1-benzyl-4-piperidinone in 100 ml of THF is then added dropwise at −60° C., and the mixture is stirred overnight while allowing the temperature to rise to rt. The reaction mixture is poured into water and extracted with ether, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H gel, eluting with DCM and then with a DCM/MeOH mixture gradient of from (99/1; v/v) to (90/10; v/v). 21.5 g of the expected product are obtained.

Workup

  1. stirringthe mixture is stirred overnight
  2. customto rise to rt
  3. extractionextracted with ether
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica H gel
  8. washeluting with DCM

Sources & evidence

ORD record
ord-7f0a1cd4c4c540cabebc7c3972625eaa
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

Loading…