N,N-Dimethylpiperidin-4-amine → HCID 59909810, compound

HRID 2182987Notes

Reaction equation

HRID 2182987 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([C:23](OCC)=[O:24])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][N:30]([CH3:37])[CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(O)C>[NH3:19].[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([C:23]([N:34]3[CH2:35][CH2:36][CH:31]([N:30]([CH3:37])[CH3:29])[CH2:32][CH2:33]3)=[O:24])[N:19]=2)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 59909797ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

Product 2

HCID 222AmmoniaHCID 59909810HCID 59909810, compoundYield 135%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (800 mg, 2.03 mmol) in ethanol (10 ml) was treated with N,N-dimethyl-N-(4-piperidinyl)amine (1.23 g, 9.61 mmol) and the resulting mixture was heated under reflux under a nitrogen atmosphere for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed sequentially with water and brine, dried over anhydrous sodium sulphate, filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (90:10) to give a residue which was further purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (90:10:0.5) to afford the title compound as a yellow oil (653 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed sequentially with water and brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (90:10)
  12. customto give a residue which
  13. customwas further purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-112fd2b59f85445eb148c88606810c02
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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