2,6-Lutidine → Ethyl 4-(3-oxopropyl)piperidine-1-carboxylate

HRID 484489Notes

Reaction equation

HRID 484489 reaction equation
Cl[C:2](=[O:16])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1.CC1C=CC=C(C)N=1.[H][H]>[Pd].O1CCCC1>[O:16]=[CH:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 14989196Ethyl 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14989197Ethyl 4-(3-oxopropyl)piperidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 102 parts of ethyl 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate, 45 parts of 2,6-dimethylpyridine and 630 parts of tetrahydrofuran was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The reside was dissolved in 650 parts of dichloromethane. The solution was washed twice with 100 parts of a hydrochloric acid solution 5% and twice with 100 parts of water, dried filtered and evaporated. The residue was distilled, yielding 71.1 parts (81%) of ethyl 4-(3-oxopropyl)-1-piperidinecarboxylate; bp. 130°-135° C. at 133 Pa (int. 46).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe reside was dissolved in 650 parts of dichloromethane
  4. washThe solution was washed twice with 100 parts of a hydrochloric acid solution 5% and twice with 100 parts of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-171b608a92034bdf8dd1f4bb141af203
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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