N-bromobutanimide → HCID 58994427, 화합물

HRID 1190156

반응식

HRID 1190156 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=O.C1C(=O)N([Br:25])C(=O)C1>CO.C(Cl)Cl.[Pd]>[Br:25][C:5]1[CH:6]=[C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][C:4]=1[NH2:1]

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 27974734-[2-(4-Nitrophenyl)ethyl]morpholine

생성물 1

HCID 58994427HCID 58994427, 화합물수율 58%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution 4-[2-(4-nitro-phenyl)-ethyl]-morpholine (0.70 g, 2.97 mmol) (as prepared in the previous step) in 15 mL of MeOH was added 10% Pd/C (30 mg) and the mixture hydrogenated under 20 psi of H2 for 2 h. The mixture was filtered though Celite and concentrated. The residue was dissolved in DCM (20 mL) and NBS (0.53 g, 2.97 mmol) was added and the reaction stirred for 20 min at RT. The reaction was diluted with DCM (20 mL) and washed with NaHCO3 (2×40 mL) and the organic layer dried over Na2SO4 and concentrated. The title compound was eluted from a 20-g SPE with 100% EtOAc to give 0.49 g (58%) of a light yellow oil. Mass spectrum (ESI, m/z): Calcd. for C12H17BrN2O, 285.0 (M+H). found 285.0.

후처리

  1. filtrationThe mixture was filtered though Celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM (20 mL)
  4. washwashed with NaHCO3 (2×40 mL)
  5. dry with materialthe organic layer dried over Na2SO4
  6. concentrationconcentrated
  7. washThe title compound was eluted from a 20-g SPE with 100% EtOAc

출처 및 근거

ORD 기록
ord-f2e24b5381cf43818a9930b175f5d492
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674100B2

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