Triethylamine → 1-[(3-Nitroquinolin-4-ylamino)methyl]cyclohexanol

HRID 44791

반응식

HRID 44791 반응식
Cl.[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].C(N(CC)CC)C.[N+](C1C=NC2C(C=1O)=CC=CC=2)([O-])=O>ClCCl.Cl.NCC1(O)CCCCC1>[N+:22]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[NH:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[CH:20][CH:19]=[CH:18][CH:17]=2)([O-:24])=[O:23]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 112758084-Chloro-3-nitroquinoline3회HCID 178526762HCID 178526762, 화합물

생성물 1

HCID 574578081-[(3-Nitroquinolin-4-ylamino)methyl]cyclohexanol수율 105.3%

시약·촉매·용매 2

HCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A suspension of 1-aminomethyl-1-cyclohexanol hydrochloride (20.0 g, 121 mmol) and 4-chloro-3-nitroquinoline (24.0 g, 115 mmol) in dichloromethane (550 mL) was cooled to 0° C., and triethylamine (40 mL, 290 mmol) was added dropwise over a period of 30 minutes. The reaction was allowed to warm to room temperature over two hours. An analysis by HPLC indicated that the 4-chloro-3-nitroquinoline starting material actually contained some 3-nitroquinolin-4-ol, and additional pure 4-chloro-3-nitroquinoline (12.0 g, 57.5 mmol) was added. The reaction was stirred for four hours, and additional 1-aminomethyl-1-cyclohexanol hydrochloride (2.0 g, 12 mmol) was added, and the resulting suspension was stirred for three days. The solvent was removed under reduced pressure, and the residue was triturated in water for one hour and isolated by filtration. The resulting solid was triturated with hot dichloromethane and isolated by filtration from the hot mixture to provide 36.5 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanol as a bright yellow powder.

후처리

  1. temperatureto warm to room temperature over two hours
  2. additionwas added
  3. stirringthe resulting suspension was stirred for three days
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was triturated in water for one hour
  6. customisolated by filtration
  7. customThe resulting solid was triturated with hot dichloromethane
  8. customisolated by filtration from the hot mixture

출처 및 근거

ORD 기록
ord-8dac8ca5e7f441478899ab7695f6fb65
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541438B2

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