Hydrochloric Acid → HCID 69092455, compound

HRID 493142Notes

Reaction equation

HRID 493142 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH2:16][CH2:15][C:14]3=[C:21]2[CH2:26][CH2:25][N:24](C(OCC3C=CC=CC=3)=O)[CH2:23][CH2:22]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)C>[OH2:8].[NH:24]1[CH2:23][CH2:22][CH:21]([C:14]2[C:13]3[C:18](=[CH:19][CH:20]=[C:11]([NH:10][S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:9])=[O:8])[CH:12]=3)[O:17][CH2:16][CH:15]=2)[CH2:26][CH2:25]1.[NH:24]1[CH2:23][CH2:22][CH:21]([C:14]2[C:13]3[C:18](=[CH:19][CH:20]=[C:11]([NH:10][S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:9])=[O:8])[CH:12]=3)[O:17][CH2:16][CH:15]=2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 69060409HCID 69060409, compound

Product 1

HCID 69092455HCID 69092455, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of benzyl 4-{6-[(phenylsulfonyl)amino]-2,3-dihydro-4H-chromen-4-ylidene}piperidine-1-carboxylate (500 mg, 1 mmol), ethanol (2 mL) and 6N hydrochloric acid (18 mL) is heated at reflux temperature for 2 hours, cooled to 0°-5° C., treated with 6N sodium hydroxide (14 mL) with cooling, then with saturated aqueous sodium carbonate to pH 9 and with chloroform. The organic phase is dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethanol to afford the title compound as an off-white solid, 75 mg (20% yield), mp >230° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. temperaturecooled to 0°-5° C.
  4. temperaturewith cooling
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is crystallized from ethanol

Sources & evidence

ORD record
ord-817d2ac46b0f4d299284cecfe7e1fe03
Source dataset
uspto-grants-2009_05
Patent number
US07534801B2

Reaction notes

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