Thionyl Chloride → 3-(2-Chloroethyl)-1,4-dimethyl-2-piperazinone

HRID 1979813Notes

Reaction equation

HRID 1979813 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH:8]1[N:13]([CH3:14])[CH2:12][CH2:11][N:10]([CH3:15])[C:9]1=[O:16].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:3][CH2:6][CH2:7][CH:8]1[N:13]([CH3:14])[CH2:12][CH2:11][N:10]([CH3:15])[C:9]1=[O:16]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 133767393-(2-Hydroxyethyl)-1,4-dimethyl-2-piperazinone

Product 1

HCID 133767413-(2-Chloroethyl)-1,4-dimethyl-2-piperazinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.5 mL) was added dropwise to an ice cooled methylene chloride (5 mL) solution of 3-(2-hydroxyethyl)-1,4-dimethyl-2-piperazinone (0.40 g, described in Example 1). The reaction mixture was stirred for 30 min and poured on an ice solution of 10% sodium bicarbonate. The mixture was extracted with methylene chloride, and the organic extract was dried and evaporated to give the title compound: IR (CHCl3) 1635 cm-1 ; and NMR (CDCl3) δ 2.35 (s, 3H) and 2.90 (s, 3H).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. extractionthe organic extract
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-99aeb12ef8364fc3beb4d1e190749932
Source dataset
uspto-grants-1984_11
Patent number
US04482714

Reaction notes

Loading…