Hydrochloric Acid → HCID 25219319, compound

HRID 1500318Notes

Reaction equation

HRID 1500318 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[C-:21]#[N:22].[K+]>C(O)C.O.C(OCC)(=O)C.CCOC(C)=O.CCCCCCC>[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)([C:21]#[N:22])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 192201-Benzyl-4-piperidoneHCID 31268Pyrrolidine

Product 1

HCID 25219319HCID 25219319, compoundYield 98.4%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

100 g (5 eq) pyrrolidine were added to a solution of 50 g (1 eq) 1-benzylpiperidin-4-one in 250 ml ethanol and the mixture was stirred for 10 min at room temperature. 25 ml (0.5 eq) hydrochloric acid were then added dropwise to the reaction mixture over a period of 10 min and the mixture was stirred for 30 min at room temperature. 55 g (3 eq) potassium cyanide dissolved in 250 ml water were added to this reaction mixture and it was stirred for three days at room temperature. The reaction course was monitored by thin-layer chromatography (50% EtOAc/heptane). Once the conversion was complete, the solid that had formed was filtered off and washed with iced water (3×150 ml). The solid obtained was then suspended in ethyl acetate and dried with Na2SO4. Following removal of the solvent under reduced pressure, 70 g of crude product were obtained in the form of a solid.

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. additionwere added to this reaction mixture and it
  3. stirringwas stirred for three days at room temperature
  4. customthe solid that had formed
  5. filtrationwas filtered off
  6. washwashed with iced water (3×150 ml)
  7. customThe solid obtained
  8. dry with materialdried with Na2SO4
  9. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-fb56a8d5eced474cb23657fd98c5d30a
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

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