Isopropanol → 6-(3-Methoxyphenyl)-4-Propylmorpholin-3-one

HRID 2102341노트

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HRID 2102341 반응식
[OH-].[K+].C(O)(C)C.Cl[CH2:8][C:9]([N:11]([CH2:15][CH:16]([OH:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[CH2:12][CH2:13][CH3:14])=[O:10]>O>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:16]2[CH2:15][N:11]([CH2:12][CH2:13][CH3:14])[C:9](=[O:10])[CH2:8][O:25]2)[CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 574406812-Chloro-N-[2-hydroxy-2-(3-methoxyphenyl)ethyl]-N-propylacetamide

생성물 1

HCID 150064786-(3-Methoxyphenyl)-4-Propylmorpholin-3-one수율 100%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Potassium hydroxide (4.2 g, 0.07 mol), isopropyl alcohol (500 ml) and the amide from example 4 (17.8 g, 0.06 mol) were stirred together as an opaque solution with water (15 ml) for 2 hours. The reaction mixture was concentrated in vacuo and the yellow residue dissolved in ethyl acetate (200 ml. This was partitioned with water (200 ml) then brine (200 ml). The organic fraction was dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow oil (15.8 g, 0.06 mol, 100%). 1H NMR (CDCl3, 400 MHz) δ: 0.96 (t, 3H), 1.62 (m, 2H), 3.36 (m, 2H), 3.51 (q, 2H), 3.81 (s, 3H), 4.30-4.62 (bq, 2H), 4.79 (d, 1H), 6.85 (d, 1H), 6.91 (d, 1H), 6.95 (s, 1H), 7.29 (t, 1H). LRMS: m/z 272. Analysis found C, 66.80; H, 7.78; N, 5.52%. C14H19NO3.0.1H2O requires C, 66.96; H, 7.71; N, 5.58%.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe yellow residue dissolved in ethyl acetate (200 ml
  3. customThis was partitioned with water (200 ml)
  4. dry with materialThe organic fraction was dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6922ce224daf4d919422a453cbb12fa3
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576081B2

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