Water → (+)-3-[6-(7-Chloroquinolin-2-ylmethoxy)chroman-3-ylmethyl]phenylamine

HRID 1684635노트

반응식

HRID 1684635 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[CH:13]=2)[O:8][CH2:7]1.[H-].[Na+].Cl[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][C:28]([Cl:34])=[CH:29][CH:30]=2)[N:25]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:34][C:28]1[CH:27]=[C:26]2[C:31]([CH:32]=[CH:33][C:24]([CH2:23][O:16][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH2:7][CH:6]([CH2:5][C:4]3[CH:3]=[C:2]([NH2:1])[CH:19]=[CH:18][CH:17]=3)[CH2:15]4)=[N:25]2)=[CH:30][CH:29]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 109548447-Chloro-2-(chloromethyl)quinolineHCID 19039972(+)-3-(3-Aminobenzyl)chroman-6-ol

생성물 1

HCID 19039973(+)-3-[6-(7-Chloroquinolin-2-ylmethoxy)chroman-3-ylmethyl]phenylamine수율 81%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 350 mg (1.37 mmole) of the product from Example 140 in 10 mL dimethylformamide at 0° C. was added 60 mg (1.51 mmole) sodium hydride. The mixture was stirred at 0° C. for 30 minutes, then 349 mg (1.64 mmole) 2-(chloromethyl)-7-chloroquinoline was added. The mixture was warmed to room temperature and stirred for 72 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 40% ethyl acetate in hexanes yielded 476 mg (81%) of the title product as a solid, mp 128°-130° C. Analysis calculated for C26H23N2O2Cl: C, 72.47; H, 5.38; N, 650. Found: C, 72.47; H, 5.12; N, 6.43.

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 72 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil

출처 및 근거

ORD 기록
ord-84635348c31b4f9ebd4573e0fe4059f1
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05641789

반응 노트

불러오는 중…