1-Methylpiperazine → 1-{[4-(2-Methoxy-5-nitrophenyl)furan-2-yl]methyl}-4-methylpiperazine

HRID 1593789노트

반응식

HRID 1593789 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[CH:13]=[C:14]([CH:17]=O)[O:15][CH:16]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CN1CCCC1=O.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]1[CH:13]=[C:14]([CH2:17][N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)[O:15][CH:16]=1

참가 물질

7

반응물 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 160991814-(2-Methoxy-5-nitrophenyl)furan-2-carbaldehyde

생성물 1

HCID 160991751-{[4-(2-Methoxy-5-nitrophenyl)furan-2-yl]methyl}-4-methylpiperazine수율 18.5%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
0 °C

실험 절차

A mixture of 4-(2-methoxy-5-nitrophenyl)-2-furaldehyde (230 mg, 0.93 mmol) and N-methylpiperazine (0.90 mL, 8.1 mmol) in 20 mL of dichloromethane and 2 mL of 1-methylpyrolidinone was cooled to 0° C. Sodium triacetoxyborohydride (1.21 g, 5.7 mmol) was added in portions followed by a few drops of acetic acid. The resulting mixture was stirred at 0° C. for 10 minutes then at room temperature for 1.5 hours. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with a gradient of 20% methanol in ethyl acetate to 1% ammonium hydroxide in 20% methanol in ethyl acetate. Trituration with diethyl ether and hexane provided 57 mg (18%) of 1-{[4-(2-methoxy-5-nitrophenyl)-2-furyl]methyl}-4-methylpiperazine as a light yellow solid, 1H NMR (DMSO-d6) δ 2.14 (s, 3H), 2.25-2.36 (broad s, 4H), 2.38-2.46 (broad s, 4H), 3.52 (s, 2H), 4.04 (s, 3H), 6.96 (s, 1H), 7.31 (d, J=8 Hz, 1H), 8.14-8.20 (m, 2H), 8.38 (d, J=3 Hz, 1H); MS 332.1 (M+H)+.

후처리

  1. waitat room temperature for 1.5 hours
  2. customThe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography
  7. washeluting with a gradient of 20% methanol in ethyl acetate to 1% ammonium hydroxide in 20% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-b079a27d5c85452e904acf7a00b043ef
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297795B2

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