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

HRID 2082553Notes

Reaction equation

HRID 2082553 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8223c9b8d7a248b3b3e08493fc7f32fc
Source dataset
uspto-grants-1993_02
Patent number
US05189179

Reaction notes

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