Butylamine → Methyl 3-[(butylamino)methyl]-5-methylbenzoate

HRID 14143

反応式

HRID 14143 の反応式
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>C(Cl)Cl>[CH2:26]([NH:30][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH2:27][CH2:28][CH3:29]

参加物

6

反応物 4

HCID 8007ButylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

生成物 1

HCID 21086163Methyl 3-[(butylamino)methyl]-5-methylbenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To an ice-cold, stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.1 mmol) in methylene chloride (2.2 mL) is added triethylamine (0.304 mL, 2.2 mmol) followed by methanesulfonyl chloride (0.116 mL, 1.5 mmol). The reaction mixture is stirred for 15 min and filtered. Butylamine (0.543 mL, 5.5 mmol) is added to the filtrate, and the reaction mixture is stirred at room temperature for 5 h. The reaction mixture is diluted with methylene chloride (10 mL), washed with 1 N hydrochloric acid, and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 89:10:1 chloroform/methanol/ammonium hydroxide) provides the title compound. 1H NMR (300 MHz, CDCl3) δ 7.75 (s, 1H), 7.70 (s, 1H), 7.24 (br s, 1H), 4.42 (d, J=9 Hz, 2H), 3.90 (s, 3H), 3.16 (m, 2H), 2.38 (s, 3H), 1.64 (s, 2H), 1.44 (m, 9H), 1.27 (m, 2H), 0.89 (t, J=7 Hz, 3H).

後処理

  1. filtrationfiltered
  2. stirringthe reaction mixture is stirred at room temperature for 5 h
  3. washwashed with 1 N hydrochloric acid, and saturated sodium bicarbonate
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 89:10:1 chloroform/methanol/ammonium hydroxide)

出典と根拠

ORDレコード
ord-da889acc1e3b408ab042d971a49859b8
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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