Methyl Ethyl Ketone → 1-Decylpiperazine

HRID 704390Notes

Reaction equation

HRID 704390 reaction equation
[N:1]1([C:7](OCC)=O)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]C.CC(=O)CC>O>[CH2:7]([N:1]1[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Conditions

Temperature
80 °C

Procedure

A mixture of 2.02 g of ethyl 1-piperazinecarboxylate, 1.92 g of anhydrous potassium carbonate, 3.08 g of decyl bromide and 20 ml of 2-butanone was stirred overnight at 80° C. After addition of water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was extracted with 3N hydrochloric acid. The extract was made alkaline with potassium carbonate and then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure Ethanol (20 ml) and ml of 10% aqueous sodium hydroxide were added to the residue, and the mixture was stirred overnight at 100° C. The reaction mixture was cooled and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.38 g of 1-decylpiperazine as an oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. extractionThe ethyl acetate layer was extracted with 3N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure Ethanol (20 ml) and ml of 10% aqueous sodium hydroxide
  7. additionwere added to the residue
  8. stirringthe mixture was stirred overnight at 100° C
  9. temperatureThe reaction mixture was cooled
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-980ac44357c1462e92d5e2bec476cd14
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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