Benzylamine → Benzyl-(3-methoxy-4-nitro-benzyl)amine

HRID 1830780노트

반응식

HRID 1830780 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6]Br.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 126216043-Methoxy-4-nitrobenzyl bromide

생성물 1

HCID 22046378Benzyl-(3-methoxy-4-nitro-benzyl)amine수율 73.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 150 mL round bottomed flask containing 1.97 g (8.0 mmol) of 3-methoxy-4-nitro-benzyl bromide in 20 mL THF was added, 2.4 g (24 mmol, 3eq.) of triethylamine followed by 2.5 g (24 mmol, 3 eq.) of benzylamine. The mixture was stirred at room temperature for 2 h, and was then partitioned between 50 mL ethyl acetate and brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 1-4% MeOH in dichloromethane to give 1.6 g (73%) of the benzyl amine as a yellow oil. 1H NMR (400 MHz, CDCl3): δ7.84 (d, J=8.61 Hz, 1H), 7.34 (m, 5H), 7.16,(s, 1H), 6.99 (d,J=8.61 Hz, 1H), 3.97 (s, 3H), 3.86 (s, 2H), 3.81 (s, 2H).

후처리

  1. additionwas added
  2. customwas then partitioned between 50 mL ethyl acetate and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 1-4% MeOH in dichloromethane

출처 및 근거

ORD 기록
ord-4fa6e59b23944990a8818cd12ee40d94
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067506B2

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