Acetone → HCID 12374090, compound

HRID 1075814Notes

Reaction equation

HRID 1075814 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1.O=S(Cl)[Cl:12].O.CC(C)=O>C(=O)=O>[ClH:12].[ClH:12].[Cl:12][CH2:2][CH2:3][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 24386Thionyl ChlorideHCID 91308Piperazineethanol

Product 1

HCID 12374090HCID 12374090, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

(E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966).) To 25.0 g (0.192 mol) of 2-(2-hydroxyethyl)piperazine, chilled in dry ice, 125 ml SOCl2 was cautiously added dropwise. After addition was complete, the mixture was cautiously heated on a steam bath with stirring for 2 hr. The reaction was cooled and treated cautiously with H2O until a solution resulted. The reaction was evaporated to dryness, and the dark residue was redissolved in H2O and filtered. The dark filtrate was heated on the steam bath with decolorizing carbon for 30 min and filtered to yield a pale yellow solution. Acetone was added to precipitate the product in two crops: 29.3 g white solid, mp 336°-339° dec., and 11.6 g (total 96% yield) pale-yellow solid, mp 330°-350° dec. (E. F. Rogers and H. J. Becker, U.S. Pat. No. 3,281,423 (1966) mp 348°-350° dec.)

Workup

  1. additionAfter addition
  2. temperaturethe mixture was cautiously heated on a steam bath
  3. temperatureThe reaction was cooled
  4. customresulted
  5. customThe reaction was evaporated to dryness
  6. dissolutionthe dark residue was redissolved in H2O
  7. filtrationfiltered
  8. temperatureThe dark filtrate was heated on the steam bath with decolorizing carbon for 30 min
  9. filtrationfiltered
  10. customto yield a pale yellow solution
  11. customto precipitate the product in two crops

Sources & evidence

ORD record
ord-b4ae13f96b0147338f6e917f9b21766f
Source dataset
uspto-grants-1976_05
Patent number
US03954766

Reaction notes

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