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

HRID 981635Notes

Reaction equation

HRID 981635 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-ff29cab6af014747a6eab0ce0b5226a3
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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