Dimethylformamide → (+/-)-1-[(4-Chlorobenzyl)morpholin-2-yl]-2-(2-methoxyphenyl)-ethene oxalic acid salt

HRID 1532994

반응식

HRID 1532994 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][CH2:8]C[OH:10])=[CH:4][CH:3]=1.[C:13]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][O:21][C:22](=O)[CH3:23])(=[O:15])C.C(N(CC)CC)C.I[C:33]1[CH:38]=[CH:37][CH:36]=C[C:34]=1[O:39][CH3:40].C(N(C(C)C)CC)(C)C.CN([CH:53]=[O:54])C>C1COCC1.CCOCC>[C:53]([OH:54])(=[O:10])[C:13]([OH:16])=[O:15].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:23][CH2:22][O:21][CH:20]([CH:19]=[CH:18][C:17]3[CH:36]=[CH:37][CH:38]=[CH:33][C:34]=3[O:39][CH3:40])[CH2:8]2)=[CH:11][CH:12]=1

참가 물질

9

반응물 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 68257o-IodoanisoleHCID 81531DiisopropylethylamineHCID 4244522-(4-Chloro-benzylamino)-ethanolHCID 643799(2Z)-but-2-ene-1,4-diyl diacetate

생성물 1

HCID 69687101(+/-)-1-[(4-Chlorobenzyl)morpholin-2-yl]-2-(2-methoxyphenyl)-ethene oxalic acid salt

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
130 °C

실험 절차

A mixture of N-(4-chlorobenzyl)-N-(2-hydroxyethyl) amine (2.00 g, 10.8 mmol) and cis-1,4-diacetoxy-2-buten (2.78 g, 16.2 mmol), triethylamine (3.26 g, 32.3 mmol), tetrakis triphenylphosphino palladium(O) (0.31 g, 0.27 mmol) in THF (20 ml) was refluxed overnight. DMF (10 ml) was added and the THF was stripped off in vacuum. Addition of 2-iodoanisole (3.8 g, 16.2 mmol) and diisopropylethylamine (2.8 g, 21.6 mmol) was followed by heating to 130° C. overnight. Ether was added and the organics were washed twice with aqueous sodium hydroxide (1 M). Chromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base. Dissolution in ether and precipitation with oxalic acid gave the title compound. Yield 1.0 g, 21%. mp 178-180° C.

후처리

  1. temperaturewas refluxed overnight
  2. washthe organics were washed twice with aqueous sodium hydroxide (1 M)
  3. customChromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base
  4. customprecipitation with oxalic acid

출처 및 근거

ORD 기록
ord-5f20e29e5b034c86b77ca0e8bd73a0a0
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207662B1

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