Morpholine → Methyl 3-(morpholin-4-yl)phenylacetate

HRID 1017565

반응식

HRID 1017565 반응식
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:13]1([C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

참가 물질

7

반응물 3

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 11746402Methyl 2-(3-bromophenyl)acetate

생성물 1

HCID 18403524Methyl 3-(morpholin-4-yl)phenylacetate수율 23%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
100 °C

실험 절차

A round bottom flasked flushed with argon was charged with methyl 3-bromophenyl-acetate (2.29 g, 10 mmol) (prepared from 3-bromophenylacetic acid as described in example 2, step 1), morpholine (1.05 mL, 1.2 eq.), CsCO3 (4.55 g, 1.4 eq.), Pd2(dba)3 (92 mg, 0.01 eq) and BINAP (93 mg, 0.15 eq.) in toluene (20 mL). The resulting mixture was heated at 100° C. overnight and then diluted with diethyl ether (120 mL). The precipitates were filtered through a Celite pad and the filtrate was concentrated and purified on a silica-gel column with 20% EtOAc in hexane to give methyl 3-(morpholin-4-yl)phenylacetate (0.55 g, 23%).

후처리

  1. customA round bottom flasked flushed with argon
  2. filtrationThe precipitates were filtered through a Celite pad
  3. concentrationthe filtrate was concentrated
  4. custompurified on a silica-gel column with 20% EtOAc in hexane

출처 및 근거

ORD 기록
ord-d77f8454ac2a429885df267293caef92
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479490B2

연결된 노트

불러오는 중…