Triethylamine → Methyl 3-methyl-5-{[methyl(pentyl)amino]methyl}benzoate

HRID 348927

반응식

HRID 348927 반응식
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.[CH3:26][NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[CH3:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH2:2][N:27]([CH3:26])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117479N-MethylpentylamineHCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

생성물 1

HCID 21086189Methyl 3-methyl-5-{[methyl(pentyl)amino]methyl}benzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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. N-Methylpentylamine (333 mg, 3.3 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, 15% ethyl acetate/hexanes) provides the title compound. 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=4 Hz, 2H), 7.36 (s, 1H), 3.90 (s, 3H), 3.47 (s, 2H), 3.13 (t, J=9 Hz, 3H), 2.39 (s, 2H), 2.34 (d, J=8 Hz, 2H), 2.18 (s, 3H), 1.45 (m, 5H), 1.32 (m, 2H).

후처리

  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, 15% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-b822f997890e44c6a04e0782ebd42209
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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