Dichloromethane → HCID 14989223, compound

HRID 981638Notes

Reaction equation

HRID 981638 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16]O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[Cl:18]CCl.S(Cl)(Cl)=O>O>[Cl:18][CH2:16][CH2:15][CH:12]1[CH2:13][CH2:14][N:9]([C:6]2[N:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 14989222HCID 14989222, compound

Product 1

HCID 14989223HCID 14989223, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7.3 parts of 1-(6-methoxy-3-pyridazinyl)-4-piperidineethanol in 130 parts of dichloromethane was added dropwise to 7.3 parts of thionyl chloride at room temperature. Upon complete addition, stirring was continued overnight at room temperature. The residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding a first fraction of 1.8 parts of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methoxypyridazine. The aqueous layer was neutralized with an ammonium hydroxide solution. The precipitated product was filtered off and taken up in dichloromethane. The organic layer was dried, filtered and evaporated, yielding a second fraction of 4.0 parts of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methoxypyridazine. Total yield: 5.8 parts (73.4%) of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methoxypyridazine as a residue (int. 96).

Workup

  1. additionUpon complete addition
  2. extractionthe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3e2b023b004a4f4982878f480f263df2
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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