2-(2-Chlorophenoxymethyl)oxirane → N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride

HRID 1656646

반응식

HRID 1656646 반응식
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[CH2:3]1.[Cl:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[O:16][CH2:17][CH:18]1[O:20][CH2:19]1>C(O)C>[ClH:13].[OH:12][C:6]1[CH:5]=[C:4]2[C:9]([CH2:10][CH2:11][CH:2]([NH:1][CH2:19][CH:18]([OH:20])[CH2:17][O:16][C:15]3[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=3[Cl:13])[CH2:3]2)=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 1375002-(2-Chlorophenoxymethyl)oxiraneHCID 109427847-Amino-5,6,7,8-tetrahydronaphthalen-2-ol

생성물 1

HCID 19788315N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride수율 100.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-amino-7-hydroxytetralin (1.9 g) and 1-(2-chlorophenoxy)-2,3-epoxypropane (2.15 g) in absolute ethanol (60 ml) is refluxed for 5 hours and then ethanol is evaporated off under reduced pressure. The thus obtained residue is chromatographed on a silica gel column eluting first with ethyl acetate up to the complete elution of the first spot and then with a mixture ethyl acetate/methanol 9/1 v/v. The obtained fractions are pooled and concentrated to dryness. The residue is dissolved in isopropanol (20 ml) and the obtained solution is acidified by the addition of HC1/isopropanol. The precipitate is recovered by filtration yielding 2.25 g of N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride; m.p. 201°-203° C.

후처리

  1. temperatureis refluxed for 5 hours
  2. customethanol is evaporated off under reduced pressure
  3. customThe thus obtained residue is chromatographed on a silica gel column
  4. washeluting first with ethyl acetate up to the complete elution of the first spot
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue is dissolved in isopropanol (20 ml)
  7. additionthe obtained solution is acidified by the addition of HC1/isopropanol
  8. filtrationThe precipitate is recovered by filtration

출처 및 근거

ORD 기록
ord-e098c31bbd3d47c7aca3880fe4654525
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254595

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