Tributylphosphine → HCID 18760290, compound

HRID 432813Notes

Reaction equation

HRID 432813 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](Cl)=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](P(CCCC)CCCC)[CH2:19][CH2:20]C.C([Mg]Cl)CC>O1CCCC1>[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](=[O:16])[CH2:18][CH2:19][CH3:20])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 15718173N-benzoylnipecotoyl chlorideHCID 178455855HCID 178455855, compound

Product 1

HCID 18760290HCID 18760290, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

1-benzoyl-3-piperidinecarbonyl chloride (1.01 g; 4.02 mmol) was dissolved in dry tetrahydrofuran (30 ml) under a nitrogen atmosphere, and cooled to −20° C. Tributylphosphine (1.1 ml; 4.4 mmol) was then added and after 20 minutes of stirring at −20° C., propylmagnesium chloride (2 ml; 4.0 mmol; 2 M in ether) was added. After stirring for 5 minutes, the reaction was quenched by addition of 1 N HCl (5 ml), and the mixture was allowed to warm to ambient temperature. It was then diluted with 1 N HCl and extracted with diethyl ether. The ether was washed with saturated sodium bicarbonate solution, and then brine. It was then dried with anhydrous magnesium sulfate and evaporated at ambient temperature under reduced pressure. The crude product was purified by chromatography on silica eluting with 50% ethyl acetate in hexane, giving 1-benzoyl-3-butyrylpiperidine (401.7 mg) as a colorless oil. MS m/z (positive ion) 260 (MH+; 100).

Workup

  1. stirringAfter stirring for 5 minutes
  2. customthe reaction was quenched by addition of 1 N HCl (5 ml)
  3. temperatureto warm to ambient temperature
  4. additionIt was then diluted with 1 N HCl
  5. extractionextracted with diethyl ether
  6. washThe ether was washed with saturated sodium bicarbonate solution
  7. dry with materialIt was then dried with anhydrous magnesium sulfate
  8. customevaporated at ambient temperature under reduced pressure
  9. customThe crude product was purified by chromatography on silica eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cf5359c5a6994b008f9bc1e232310186
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Reaction notes

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