Ammonia → 3-(Phenylmethyl)-2-piperidinone

HRID 1955698

Reaction equation

HRID 1955698 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[O:21])C=CC=CC=1.N>C1COCC1>[C:15]1([CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][C:9]2=[O:21])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 110871491,3-Diphenylmethyl-2-piperidinone

Product 1

HCID 44389953-(Phenylmethyl)-2-piperidinoneYield 146.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,3-diphenylmethyl-2-piperidinone (2.79 g, 10 mmol) in dry THF (25 mL) was added at -78° C. to a well stirred solution of Li metal (0.70 g, 100 mmol) in liquid NH3 (200 mL). After 15 min, the cooling bath was removed, and the NH3 was allowed to escape (ca. 2 h). The resulting colorless residue was treated with saturated NH4Cl (50 mL), and extracted with EtOAc (3×50 mL). The combined organic extract was washed with brine (25 mL), dried over MgSO4, and concentrated in vacuo to give 2.78 g of brown viscous residue. Flash chromatography over silica gel (1% MeOH in CHCl3 -EtOAc, 1:1) afforded the lactam (See: Rodriquez m, Heitz A, Martinez J (1992) supra) (0.87 g, 46% ) as a colorless solid: mp 120°-122° C. (CH2Cl2 -hexanes).

Workup

  1. customthe cooling bath was removed
  2. custom(ca. 2 h)
  3. additionThe resulting colorless residue was treated with saturated NH4Cl (50 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. extractionThe combined organic extract
  6. washwas washed with brine (25 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dfe3ad210be48ab826149a990ccd081
Source dataset
uspto-grants-1998_07
Patent number
US05776959

Linked notes

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