Azepane → HCID 16775581, compound

HRID 2252537Notes

Reaction equation

HRID 2252537 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[NH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1(C)C(C)=CC=CC=1.CCCCCC>[N:11]1([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 8119AzepaneHCID 792226-Chloronicotinic acid

Product 1

HCID 16775581HCID 16775581, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8058HexaneSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 6-chloronicotinic acid (5.0 g) and perhydroazepine (7.16 mL) in xylene (20 mL) was stirred at 140° C. for 30 hours under an atmosphere of argon. The reaction mixture was cooled to room temperature, diluted with hexane and filtrated. The insoluble material was dissolved in ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous magnesium sulfate and concentrated to give the title compound (3.19 g) having the following physical data.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltrated
  3. dissolutionThe insoluble material was dissolved in ethyl acetate
  4. washThe organic layer was washed with water and brine sequentially
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad77aa8a2aec48039e6839591256fd0f
Source dataset
uspto-grants-2008_01
Patent number
US07323456B2

Reaction notes

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