Sulfuric Acid → 1-[(cis)-4-(3,4-Dichlorobenzyl)-5-methylmorpholin-2-yl]methanamine

HRID 2211967

반응식

HRID 2211967 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:5][NH:6][CH:7]([CH3:10])[CH2:8][OH:9].O1[CH2:17][CH:16]1[CH2:18][N:19]1C(=O)C2C(=CC=CC=2)C1=O.S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:5][N:6]1[C@H:7]([CH3:10])[CH2:8][O:9][C@H:16]([CH2:18][NH2:19])[CH2:17]1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 219629772-{[(3,4-Dichlorophenyl)methyl]amino}propan-1-ol

생성물 1

HCID 695074021-[(cis)-4-(3,4-Dichlorobenzyl)-5-methylmorpholin-2-yl]methanamine수율 72.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of Intermediate 4 (0.470 g) and 2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.410 g) was heated at 80° C. under nitrogen for 5 h. The mixture was treated with concentrated sulphuric acid (0.6 ml) then stirred at 150° C. for 42 h. The mixture was treated with water (50 ml) then washed with ethyl acetate (2×50 ml). The dark aqueous phase was basified to ˜pH 11 using 5M aqueous sodium hydroxide then extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with water and brine, dried (Na2SO4) and concentrated under vacuum to give the title compound as a brown oil (0.42 g).

후처리

  1. washthen washed with ethyl acetate (2×50 ml)
  2. extractionthen extracted with ethyl acetate (2×50 ml)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-bd31778a81e84adb92828a916c1f8897
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101882B2

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