Pyridine → HCID 58494869, compound

HRID 516248Notes

Reaction equation

HRID 516248 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:29][C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[Cl:29][C:30]([N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 66982459HCID 66982459, compound

Product 1

HCID 58494869HCID 58494869, compoundYield 193.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.83 g of t-butyl 1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 40 ml of dichloromethane were added 1.3 ml of pyridine and 1.29 g of triphosgene under ice-cooling, followed by stirring for 3 hours. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed with water and an aqueous ammonium chloride solution, dried over anhydrous magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. To the residue was added hexane, followed by stirring, and the solid was collected by filtration and dried to obtain 3.07 g of t-butyl 1-(chlorocarbonyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a white solid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialan aqueous ammonium chloride solution, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionTo the residue was added hexane
  9. stirringby stirring
  10. filtrationthe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-39dd75fec5cb408595a1757a6e604813
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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