Ammonia → 3-(Phenylmethyl)-2-piperidinone

HRID 1955698

반응식

HRID 1955698 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8dfe3ad210be48ab826149a990ccd081
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05776959

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