Hydrochloric Acid → HCID 131717788, compound

HRID 273811Notes

Reaction equation

HRID 273811 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])[CH2:11][CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:5][CH:4]=1.[C:20]([BH3-])#[N:21].[Na+].[C:24](=[O:27])(O)[O-].[Na+].[ClH:29].[CH2:30](O)[CH3:31]>CO.O>[ClH:29].[OH:27][C:24]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:9][CH:10]=[C:30]2[CH2:31][CH2:20][NH:21][CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=1)=[O:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 13974528HCID 13974528, compound

Product 1

HCID 131717788HCID 131717788, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
23 °C

Procedure

Serotonin hydrochloride hemihydrate (200 mg) and N-[4-(trifluoromethyl)phenyl]-5-oxo-hexanamide (246 mg) were stirred under nitrogen in methanol (8 mL) and treated with sodium cyanoborohydride (85 mg). After stirring 66 hours at 23° C., sodium bicarbonate (250 mg) and water (5 mL) were added. Thirty minutes later, the reaction was diluted with water (50 mL) and extracted with 1:4 2-propanol:dichloromethane (40 mL, 40 mL, 20 mL) and the extracts dried (Na2SO4) and concentrated in vacuo to an oil. The oil was chromatographed with 5:10:90, then 3:50:50 triethylamine:ethanol:ethyl acetate to isolate a component with Rf of 0.15 (5:10:90 triethylamine:ethanol:ethyl acetate). This oil was dissolved in ethanol (50 mL), treated with 1:9 concentrated hydrochloric acid:ethanol (2 mL), and concentrated in vacuo. Reconcentration from ethanol (50 mL) and placing under vacuum gave the title compound as an off-white solid (272 mg).

Workup

  1. extractionextracted with 1:4 2-propanol
  2. dry with materialdichloromethane (40 mL, 40 mL, 20 mL) and the extracts dried (Na2SO4)
  3. concentrationconcentrated in vacuo to an oil
  4. customThe oil was chromatographed with 5:10:90
  5. custom3:50:50 triethylamine:ethanol:ethyl acetate to isolate a component with Rf of 0.15 (5:10:90 triethylamine:ethanol:ethyl acetate)
  6. concentrationethanol (2 mL), and concentrated in vacuo

Sources & evidence

ORD record
ord-8684d3f9499d4348b7513ceb68ade212
Source dataset
uspto-grants-1995_02
Patent number
US05387604

Reaction notes

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