Thionyl Chloride → 3-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazine

HRID 1030916Notes

Reaction equation

HRID 1030916 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[N:11]=[N:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19]O)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1>ClCCl>[Cl:3][CH2:19][CH2:18][CH:15]1[CH2:16][CH2:17][N:12]([C:9]2[N:10]=[N:11][C:6]([CH3:5])=[CH:7][CH:8]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 149892172-(1-(6-Methylpyridazin-3-YL)piperidin-4-YL)ethanol

Product 1

HCID 149892183-[4-(2-Chloroethyl)-1-piperidinyl]-6-methylpyridazineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled (ice bath) solution of 7.1 parts of thionyl chloride in 65 parts of dichloromethane was added dropwise a solution of 6.6 parts of 1-(6-methyl-3-pyridazinyl)-4-piperidineethanol in 195 parts of dichloromethane. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was washed with alkaline water. The separated organic layer was dried, filtered and evaporated, yielding 7.2 parts (100%) of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine as a residue (int. 84).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. washThe reaction mixture was washed with alkaline water
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7b0982b4f4ef49559c0401f5edd43096
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

Loading…