Dimethyl Sulfoxide → 1-(3-Phenylpropionyl)-4-ketopiperidine

HRID 49445

Reaction equation

HRID 49445 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]1([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 221751621-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-one

Product 1

HCID 178176121-(3-Phenylpropionyl)-4-ketopiperidineYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To 1.68 mL of oxalyl chloride (19.2 mmol) in 35 mL of CH2Cl2 at −78° C. was added 2.73 mL (38.5 mmol) of dry DMSO in 5 mL of CH2Cl2. After the addition, 3.6 g (15.4 mmol) of 1-(3-phenylpropionyl)-4-hydroxypiperidine 134 in 5 mL of CH2Cl2 was added, and the mixture was stirred for 5 min in the cold. 10.73 mL (77 mmol) of triethylamine in 5 mL of CH2Cl2 was added, and the mixture was allowed to come to room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution. The organic phase was washed with water twice, with saturated brine, dried, and evaporated under vacuum to give 3.2 g (89%) of 1-(3-phenylpropionyl)-4-ketopiperidine (135). GC/MS showed 100% purity with a molecular ion of 231.

Workup

  1. additionwas added
  2. customto come to room temperature
  3. customThe mixture was quenched with saturated aqueous ammonium chloride solution
  4. washThe organic phase was washed with water twice
  5. dry with materialwith saturated brine, dried
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-c33b19de490b422a85936f15e5cda45d
Source dataset
uspto-grants-2004_03
Patent number
US06706740B2

Linked notes

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