Dimethylformamide → N-(1-Ethyl-3-piperidyl)-4-(8-trifluoromethyl-4-quinolylamino)benzamide

HRID 2198487

反応式

HRID 2198487 の反応式
O.Cl.[F:3][C:4]([F:26])([F:25])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[C:10]2[NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1.CN(C)C=O.[NH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([CH2:39][CH3:40])[CH2:34]1.C(=O)([O-])[O-].[Na+].[Na+]>S(Cl)(Cl)=O.C(Cl)(Cl)Cl.O>[CH2:39]([N:35]1[CH2:36][CH2:37][CH2:38][CH:33]([NH:32][C:20](=[O:21])[C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:10]3[C:9]4[C:14](=[C:5]([C:4]([F:25])([F:26])[F:3])[CH:6]=[CH:7][CH:8]=4)[N:13]=[CH:12][CH:11]=3)=[CH:24][CH:23]=2)[CH2:34]1)[CH3:40]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 980943-amino-N-ethylpiperidineHCID 705455024-(8-Trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate

生成物 1

HCID 20520139N-(1-Ethyl-3-piperidyl)-4-(8-trifluoromethyl-4-quinolylamino)benzamide収率 37%

試薬・触媒・溶媒 3

HCID 24386Thionyl Chloride触媒HCID 962Water溶媒2 回HCID 6212Chloroform溶媒

実験手順

11.6 Grams (0.03 mole) of 4-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate were refluxed in thionyl chloride containing a few drops of dimethyl formamide for one hour. The thionyl chloride was evaporated and 50 milliliters of benzene were added and evaporated. The resulting acid chloride hydrochloride was added in portions with stirring to a cooled mixture of 3.84 grams (0.03 mole) of 3-amino-1-ethylpiperidine in 80 milliliters of chloroform and 31.8 grams (0.3 mole) of sodium carbonate in 100 milliliters of water. The product began to precipitate almost at once, and the mixture was stirred vigorously for two hours, and allowed to stand overnight. Filtration gave a solid which was stirred in water, collected and dried. The resulting solid was dissolved in an ethanol:chloroform mixture and chromatographed on an alumine column made up in chloroform. Elution with chloroform gave 4.9 grams (37%) of title compound as a pale yellow solid, melting point 177°-178° C.

後処理

  1. customThe thionyl chloride was evaporated
  2. addition50 milliliters of benzene were added
  3. customevaporated
  4. additionThe resulting acid chloride hydrochloride was added in portions
  5. customto precipitate almost at once, and the mixture
  6. waitto stand overnight
  7. filtrationFiltration
  8. customgave a solid which
  9. customcollected
  10. customdried
  11. dissolutionThe resulting solid was dissolved in an ethanol
  12. customchloroform mixture and chromatographed on an alumine column
  13. washElution with chloroform

出典と根拠

ORDレコード
ord-3328dc48c13a419da6dfce9ddbcfcab7
出典データセット
uspto-grants-1982_11
特許番号
US04357333

関連ノート

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