Sodium hydride → 4-Cyano-3-(3-morpholinopropoxy)aniline

HRID 393654노트

반응식

HRID 393654 반응식
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Cl[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[C:21]#[N:22])[NH2:17]>CN1C(=O)CCC1>[C:21]([C:20]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[O:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)#[N:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 887284-Amino-2-chlorobenzonitrileHCID 1995763-Morpholino-1-propanol

생성물 1

HCID 2328004-Cyano-3-(3-morpholinopropoxy)aniline수율 26%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
145 °C

실험 절차

Sodium hydride (2.0 g of an 85% dispersion in mineral oil, 60 mmol) was added to 4-(3-hydroxypropyl)morpholine (4.8 g, 30 mmol), (Tet. Lett. 1994, 35, 1715), in NMP (50 ml) and the mixture was stirred for 15 minutes. 3-Chloro-4-cyanoaniline (4.8 g, 30 mmol) was added and the mixture was heated at 145° C. for 6 hours. The mixture was allowed to cool and was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and then brine and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by column chromatography eluting with ethyl acetate and then methylene chloride/methanol (9/1) to give 4-cyano-3-(3-morpholinopropoxy)aniline (2.0 g, 26%) as a yellow gum.

후처리

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine and dried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by column chromatography
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-2e4886f4ee0e4197b28e11cf290a84e0
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

반응 노트

불러오는 중…