Hydrochloric Acid → HCID 131717786, compound

HRID 744688Notes

Reaction equation

HRID 744688 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=O)[CH3:17])=[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]>O.CO>[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:16]([CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol3×HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 19422061HCID 19422061, compound

Product 1

HCID 131717786HCID 131717786, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Serotonin hydrochloride hemihydrate (222 mg), N-(4-methoxyphenyl)-7-oxo-octanamide (263.3 mg), and methanol (10 mL) were stirred in the dark and the resulting solution treated with sodium cyanoborohydride (95 mg). After 4 d at ca. 22° C., sodium bicarbonate (350 mg) and water (10 mL) were added. After stirring 1.5 hours, the mixture was extracted with 1:4 2-propanol:dichloromethane (3×25 mL) and the combined extracts were dried (Na2SO4) and concentrated in vacuo. Chromatography eluting with 4:10:90, then 3:30:70 triethylamine:ethanol:ethyl acetate gave a component with an Rf of 0.3 in the latter solvent system. This oil was reconcentrated twice from ethanol (50 mL), then redissolved in ethanol (ca. 50 mL), treated with 1:9 concentrated hydrochloric acid:ethanol (1.2 mL), and reconcentrated in vacuo to a pale yellow oil which foamed to a solid. This was the title compound (352 mg), isolated as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with 1:4 2-propanol
  2. dry with materialdichloromethane (3×25 mL) and the combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. washChromatography eluting with 4:10:90
  5. custom3:30:70 triethylamine:ethanol:ethyl acetate gave a component with an Rf of 0.3 in the latter solvent system

Sources & evidence

ORD record
ord-5522a96eeaad4f8eae0630f48c88df12
Source dataset
uspto-grants-1996_09
Patent number
US05559143

Reaction notes

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