Cyproheptadine → HCID 131729110, compound

HRID 1673160Notes

Reaction equation

HRID 1673160 reaction equation
OCC1[O:8][C:7]2=[C:9]([C:17]([O:19]CC)=[O:18])[S:10][C:11]([C:12]([O:14]CC)=[O:13])=[C:6]2[O:5]C1.[OH-:22].[K+].CN1CCC(=[C:29]2[C:43]3[C:38](=[CH:39][CH:40]=CC=3)[CH:37]=[CH:36]C3C2=CC=CC=3)CC1>O>[CH2:37]([C:38]1([CH2:39][CH3:40])[CH:43]([CH2:29][OH:22])[O:5][C:6]2=[C:11]([C:12]([OH:14])=[O:13])[S:10][C:9]([C:17]([OH:19])=[O:18])=[C:7]2[O:8]1)[CH3:36]

Participants

5

Reactant 3

HCID 2913CyproheptadineHCID 14797Potassium HydroxideHCID 592947872-Hydroxymethyl-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid diethyl ester

Product 1

HCID 131729110HCID 131729110, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500 mL round bottom flask equipped with a reflux condenser 11.3 g (0.0357 mol) diethyl 2,3-dihydro-2-(hydroxymethyl)thieno[3,4-b][1,4]dioxine-5,7-dicarboxylate was combined with 12.0 g (0.214 mol) potassium hydroxide in 250 mL water. The reactin mixture was refluxed and the progress of the reaction tracked by TLC. Upon completion of the hydrolysis the reaction was concentrated to ˜100 mL. The mixture was cooled to 0 C then acidified with concentrated HCl. After allowing to warm to room temperature overnight the white solid was filtered and washed with a small amount of water. Drying under high vacuum gave 8.5 g (90%) of product as a white solid. Structure and purity were confirmed by 1H/13C NMR and LC-MS.

Workup

  1. customUpon completion of the hydrolysis the reaction
  2. concentrationwas concentrated to ˜100 mL
  3. temperatureThe mixture was cooled to 0 C
  4. filtrationwas filtered
  5. washwashed with a small amount of water
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-ca4716f36ee44b1da6b4c7f7fca1209c
Source dataset
uspto-grants-2011_08
Patent number
US07999121B2

Reaction notes

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