Hydrochloric Acid → 6-[[2-(5-Hydroxy-1H-indol-3-yl)ethyl]amino]-N-phenylheptanamide, monohydrochloride hydrate

HRID 273810

反応式

HRID 273810 の反応式
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.[ClH:14].[C:15]1([NH:21][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][C:27](=O)[CH3:28])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+].Cl>CO.O.C(O)C>[OH2:7].[ClH:14].[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][CH:27]([CH3:28])[CH2:26][CH2:25][CH2:24][CH2:23][C:22]([NH:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:30]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 160436Serotonin HydrochlorideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 19422086N-phenyl-6-oxo-heptanamide

生成物 1

HCID 1317177876-[[2-(5-Hydroxy-1H-indol-3-yl)ethyl]amino]-N-phenylheptanamide, monohydrochloride hydrate収率 176.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

Serotonin hydrochloride (1.000 g) and N-phenyl-6-oxo-heptanamide (1.289 g) were stirred in methanol (47 mL) under a nitrogen atmosphere and treated with sodium cyanoborohydride (0.444 g), excluding light from the reaction. After 4 d at ca. 23° C., a solution of sodium bicarbonate (1.00 g) in water (25 mL) was added. One hour later, the reaction was diluted with water (75 mL) and extracted with 1:4 2-propanol:dichloromethane (3×75 mL). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo to a foaming oil which was chromatographed using 5:20:80 triethylamine:ethanol:ethyl acetate, isolating the component with an Rf of 0.3. The resulting oil was twice reconcentrated in vacuo from ethanol (100 mL) and then redissolved in ethanol (100 mL). This solution was treated with 1:9 concentrated hydrochloric acid: ethanol (6 mL), concentrated in vacuo reconcentrated from ethanol (100 mL) to an oil, and the oil placed under vacuum to yield the title compound as a solid (1.80 g).

後処理

  1. customfrom the reaction
  2. extractionextracted with 1:4 2-propanol
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a foaming oil which
  6. customwas chromatographed
  7. customethanol:ethyl acetate, isolating the component with an Rf of 0.3
  8. concentrationethanol (6 mL), concentrated in vacuo

出典と根拠

ORDレコード
ord-77e8716395f14d96a5690461ff37d335
出典データセット
uspto-grants-1995_02
特許番号
US05387604

関連ノート

読み込み中…