Water → HCID 9815799, compound

HRID 432874Notes

Reaction equation

HRID 432874 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][C:6]([CH3:9])=[CH:5][CH2:4]1.N1C=CC=CC=1.Cl.[N:17]1[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1.O>ClCCl.C(OCC)(=O)C>[N:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:2][CH:3]2[CH2:8][CH2:7][C:6]([CH3:9])=[CH:5][CH2:4]2)=[O:24])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 22171686HCID 22171686, compound

Product 1

HCID 9815799HCID 9815799, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-amino-4-methylcyclohex-3-ene hydrochloride (103 mg) in dichloromethane (5 ml) were added in turn pyridine (0.14 ml), 4-pyridinecarbonyl chloride hydrochloride (0.124 g) and N,N-dimethylaminoyridine (0.11 g) at 0° C. The mixture was allowed to warm to ambient temperature and was allowed to stir for 1 hour. The reaction mixture was taken up into a mixture of water and ethyl acetate, and adjusted pH to 4.6. The separated organic layer was washed in turn with water and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give 1-(pyridin-4-ylcarbonylamino)-4-methylcyclohex-3-ene (46 mg).

Workup

  1. washThe separated organic layer was washed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-c3018bfa7ff74dbaa716dbfaaf6595a9
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

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