Diethyl Ether → N-(1-Ethyl-3-piperidyl)-2-(8-trifluoromethyl-4-quinolylamino)benzamide

HRID 2198484

반응식

HRID 2198484 반응식
O.O.Cl.[F:4][C:5]([F:27])([F:26])[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[C:11]2[NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=O.[NH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][N:31]([CH2:35][CH3:36])[CH2:30]1.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>S(Cl)(Cl)=O.C(Cl)(Cl)Cl.O>[CH2:35]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([NH:28][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[NH:16][C:11]2[C:10]3[C:15](=[C:6]([C:5]([F:26])([F:27])[F:4])[CH:7]=[CH:8][CH:9]=3)[N:14]=[CH:13][CH:12]=2)[CH2:30]1)[CH3:36]

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 980943-amino-N-ethylpiperidineHCID 705463792-(8-Trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate

생성물 1

HCID 20520121N-(1-Ethyl-3-piperidyl)-2-(8-trifluoromethyl-4-quinolylamino)benzamide수율 63%

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 24386Thionyl Chloride용매

실험 절차

11.5 Grams (0.0285 Mole) of 2-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate were refluxed in 80 milliliters of thionyl chloride for half an hour. A yellow solid precipitated. The thionyl chloride was evaporated off. The resulting acid chloride hydrochloride was added in portions with stirring to a cooled mixture of 3.84 grams (0.03 moles) of 3-amino-1-ethylpiperidine in 100 milliliters of chloroform and 31.8 grams (0.3 mole) of sodium carbonate in 100 milliliters of water. The mixture was stirred for one hour and allowed to stand overnight. The chloroform layer was separated and dried and the chloroform evaporated to give a nearly colourless solid. Trituration with ether gave a colourless solid which was recrystallized from methanol to give 7.9 grams (63% yield) of title compound, melting point 212° to 213° C.

후처리

  1. customA yellow solid precipitated
  2. customThe thionyl chloride was evaporated off
  3. additionThe resulting acid chloride hydrochloride was added in portions
  4. waitto stand overnight
  5. customThe chloroform layer was separated
  6. customdried
  7. customthe chloroform evaporated
  8. customto give a nearly colourless solid
  9. customwas recrystallized from methanol

출처 및 근거

ORD 기록
ord-1430adf7fcdc446a94db511eb348b9a1
출처 데이터셋
uspto-grants-1982_11
특허 번호
US04357333

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