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

HRID 1593789

反応式

HRID 1593789 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-b079a27d5c85452e904acf7a00b043ef
出典データセット
uspto-grants-2007_11
特許番号
US07297795B2

関連ノート

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