Hydrochloric Acid → HCID 23109904, compound

HRID 2223890Notes

Reaction equation

HRID 2223890 reaction equation
COC[O:4][CH2:5][CH:6]([CH2:38][O:39]COC)[CH2:7][CH2:8][C:9]1([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([N:23]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][N:32]=3)[C:24]([C:26]3[O:27][CH:28]=[CH:29][CH:30]=3)=[O:25])[CH2:19][CH2:18]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>CO>[OH:39][CH2:38][CH:6]([CH2:5][OH:4])[CH2:7][CH2:8][C:9]1([CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([N:23]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][N:32]=3)[C:24]([C:26]3[O:27][CH:28]=[CH:29][CH:30]=3)=[O:25])[CH2:21][CH2:22]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59714920HCID 59714920, compound

Product 1

HCID 23109904HCID 23109904, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[1-[2-[1-[4-(methoxymethoxy)-3-(methoxymethoxymethyl)butyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide (300 mg) in methanol (10 mL) was added conc. hydrochloric acid (0.17 mL) at room temperature. The solution was stirred at room temperature for 16 hours. conc. Hydrochloric acid (0.17 mL) was further added to the solution, and it was stirred at 50 ° C. for 6 hours. The solution was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution was added to the residue, and it was extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The residue was purified by chromatography [silica gel, chloroform-methanol-aqueous ammonia (90:10:0.1)]to give the title compound (260 mg).

Workup

  1. stirringwas stirred at 50 ° C. for 6 hours
  2. concentrationThe solution was concentrated under reduced pressure, saturated aqueous sodium bicarbonate solution
  3. additionwas added to the residue, and it
  4. extractionwas extracted with chloroform
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography [silica gel, chloroform-methanol-aqueous ammonia (90:10:0.1)]to

Sources & evidence

ORD record
ord-30765011bad3483faccee11603dc3d44
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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