Water → acetophenone O-[2-((morpholin-4-yl))ethyl]oxime

HRID 10176

반응식

HRID 10176 반응식
[C:1](=[N:9][OH:10])([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:2].O.Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:16]1([CH2:15][CH2:14][O:10][N:9]=[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:2])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

참가 물질

7

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 69185AcetophenonoximeHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

생성물 1

HCID 86594237acetophenone O-[2-((morpholin-4-yl))ethyl]oxime

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

반응 조건

온도
75 °C

실험 절차

To a solution of acetophenone oxime (20 g) in toluene (700 mL) was added subsequently tetrabutylammonium bromide (4.77 g), water (8 mL), 4-(2-chloroethyl)morpholine hydrochloride (30.31 g) and finally 50% sodium hydroxide (aq, 52 mL). The resulting mixture was heated at 75° C. overnight. After cooling to room temperature water was added, to dissolve all the salts, the layers were separated, and the aqueous layer was extracted with toluene. The organic layers were dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/5) to afford acetophenone O-[2-((morpholin-4-yl))ethyl]oxime as an oil. The obtained oil was dissolved in 6M HCl (aq, 500 mL) and heated under reflux for 5 hours and subsequently stirred overnight at room temperature. The mixture was extracted with ether and concentrated in vacuo. The residue was crystallized from ethanol, to afford O-[2-((morpholin-4-yl))ethyl]hydroxylamine dihydrochloride. 24.8 g (77%)

후처리

  1. additionwas added
  2. dissolutionto dissolve all the salts
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with toluene
  5. dry with materialThe organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 95/5)

출처 및 근거

ORD 기록
ord-7cdc52eb0f104415883f65036a3b8c9b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094779B2

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