Diisopropylamine → HCID 68242869, compound

HRID 1055207Notes

Reaction equation

HRID 1055207 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[CH3:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=[O:26].[C:27](OCC)(=[O:29])[CH3:28]>C1COCC1>[C:27]([CH:22]1[CH2:23][CH2:24][CH2:25][N:20]([CH3:19])[C:21]1=[O:26])(=[O:29])[CH3:28]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8058HexaneHCID 8857Ethyl AcetateHCID 13603N-Methyl-2-piperidoneHCID 178418339Butyllithium

Product 1

HCID 68242869HCID 68242869, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

20.6 g of diisopropylamine (0.2 mol) were placed in 200 ml of dry THF under nitrogen and cooled to −80° C. 80 ml n-butyllithium in hexane (2.5 M, 0.2 mol) were slowly added dropwise. After the addition it was allowed to stir for 15 min and then 22.6 g N-methyl-2-piperidone (0.2 mol) were added dropwise. The reaction mixture was stirred for 30 min and then 17.6 g of dry ethyl acetate (0.2 mol) was added. The reaction mixture with stirring overnight was allowed to warm to room temperature. The THF was removed on a rotary evaporator and the residue was taken up in 80 ml 6M HCl. The aqueous phase was extracted five times with 100 ml ethyl acetate. The combined organic layers were dried over sodium sulfate and the solvent was removed on a rotary evaporator. The product (keto form:enol form=1:1) was fractionated by distillation at 0.6 mbar and obtained as a yellowish liquid (bp 70° C.).

Workup

  1. additionAfter the addition it
  2. stirringThe reaction mixture was stirred for 30 min
  3. stirringThe reaction mixture with stirring overnight
  4. temperatureto warm to room temperature
  5. customThe THF was removed on a rotary evaporator
  6. extractionThe aqueous phase was extracted five times with 100 ml ethyl acetate
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe solvent was removed on a rotary evaporator
  9. distillationThe product (keto form:enol form=1:1) was fractionated by distillation at 0.6 mbar

Sources & evidence

ORD record
ord-44bb4ab3089a4d77b9dc3331c1c99787
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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