4-Methylmorpholine → 3-Dimethylamino-1-[[(1H)-indol 3 yl]carbonyl]piperidine

HRID 1032700ノート

反応式

HRID 1032700 の反応式
Cl.Cl.[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1.CN1CCOCC1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28](O)=[O:29])=[CH:20]1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)/C=C\C(O)=O>C(O)(C)C.CCOCC.ClCCl>[CH3:3][N:4]([CH3:11])[CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:28]([C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)=[O:29])[CH2:6]1

参加物

9

反応物 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 444266Maleic AcidHCID 14459855N,N-Dimethylpiperidin-3-amine--hydrogen chloride (1/2)

生成物 1

HCID 99035673-Dimethylamino-1-[[(1H)-indol 3 yl]carbonyl]piperidine

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-dimethylaminopiperidine dihydrochloride (1.8 g, 0.01 mol), N-methylmorpholine (2.5 g) and dichloromethane (50 ml) was stirred at ambient temperature for 1.5 h. Indole-3-carboxylic acid (1.92 g, 0.012 mol) was added, followed by dicyclohexylcarbodiimide (2.5 g) and the mixture stirred for 24 h. The mixture was filtered, the filtrate was washed thrice with 1M hydrochloric acid, the acid washings were combined, basified with ammonia and extracted with chloroform. The chloroform extract was dried and evaporated to yield the product base 1.6 g. The base was dissolved in isopropyl alcohol (20ml), acidified with maleic acid (0.72 g, 5% excess) and diluted with ether (10 ml). On standing the maleate salt crystallised and was collected by filtration, 1.04 g, mp 139-141.

後処理

  1. stirringthe mixture stirred for 24 h
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed thrice with 1M hydrochloric acid
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customwas dried
  7. customevaporated
  8. customto yield the product base 1.6 g
  9. customcrystallised
  10. filtrationwas collected by filtration, 1.04 g, mp 139-141

出典と根拠

ORDレコード
ord-fbf17b3555e84a708d574706ac6ea66c
出典データセット
uspto-grants-1990_09
特許番号
US04959375

反応ノート

読み込み中…