Hydrochloric Acid → HCID 68834821, compound

HRID 747698Notes

Reaction equation

HRID 747698 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13](=[CH:16][C:17]2[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl.CN1CCOCC1.ClC(OCC)=O.Br.[NH2:42][CH2:43][CH2:44][O:45][C:46]1[CH:47]=[C:48]([CH:51]=[CH:52][CH:53]=1)[C:49]#[N:50]>O.CN(C)C=O.C(O)C>[C:49]([C:48]1[CH:47]=[C:46]([CH:53]=[CH:52][CH:51]=1)[O:45][CH2:44][CH2:43][NH:42][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH:16]=[C:13]2[CH2:12][CH2:11][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:15][CH2:14]2)=[CH:26][CH:25]=1)#[N:50]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 10616499Methyl 4-[(1-Boc-piperidin-4-ylidene)methyl]benzoateHCID 177887733-(2-Aminoethoxy)benzonitrile hydrobromide

Product 1

HCID 68834821HCID 68834821, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6 ml of 1 N sodium hydroxide and 18 ml of ethanol were added to 331 mg (1.0 mmol) of methyl 4-[(1-t-butoxycarbonylpiperidine-4-ylidene)methyl]benzoate, and they were stirred for 18 hours. The reaction liquid was acidified with 1 N hydrochloric acid. After the extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated. 5 ml of dimethylformamide, 0.22 ml (2.0 mmol) of N-methylmorpholine and 0.10 ml (1.0 mmol) of ethyl chloroformate were added to the residue under cooling with ice, and they were stirred for 30 minutes. 243 mg (1.0 mmol) of 3-(2-aminoethoxy)benzonitrile hydrobromide was added to the resultant mixture at that temperature. The temperature was elevated to room temperature, and they were stirred for one hour. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N hydrochloric acid and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe reaction liquid
  2. extractionAfter the extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. temperatureunder cooling with ice, and they
  6. stirringwere stirred for 30 minutes
  7. customwas elevated to room temperature
  8. stirringthey were stirred for one hour
  9. customThe reaction liquid
  10. extractionAfter the extraction with ethyl acetate
  11. washthe organic layer was successively washed with water, 1 N hydrochloric acid and saturated aqueous NaCl solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-4934cc6e77884b38a0af3fbc92e69e0a
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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