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

HRID 273810

반응식

HRID 273810 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-77e8716395f14d96a5690461ff37d335
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387604

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