Triethylamine → HCID 131733336, compound

HRID 516268Notes

Reaction equation

HRID 516268 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=[O:17])[CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].[CH3:36][CH2:37][O:38][C:39]([CH3:41])=[O:40]>ClC(Cl)C>[C:34]([OH:33])(=[O:17])/[CH:35]=[CH:41]/[C:39]([OH:38])=[O:40].[N:1]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:37]([O:38][C:39]([N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:40])[CH3:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 66982459HCID 66982459, compound

Product 1

HCID 131733336HCID 131733336, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 200 mg of t-butyl 1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 2.13 ml of dichloroethane were added 0.553 ml of triethylamine and 0.19 ml of ethyl chloroformate, followed by stirring at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the reaction mixture was diluted with EtOAc, washed with 1 M hydrochloric acid, water, a 1 M aqueous sodium hydroxide solution, and saturated brine, and concentrated, and the residue was purified by silica gel column chromatography (elution solvent: HEX-EtOAc). The resulting substance was dissolved in chloroform, followed by adding 0.05 ml of trifluoroacetic acid and stirring for 30 minutes. After concentration under reduced pressure, the resultant was dissolved in EtOH, neutralized by the addition of triethylamine, and then concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (elution solvent: chloroform-MeOH-aqueous ammonia). The resulting substance was dissolved in EtOH and 76 mg of fumaric acid was added thereto. The resulting white solid was collected by filtration and dried to obtain 79 mg of ethyl 2,3,4,6,7,8,9,10-octahydro-1H-azepino[4.5-g]quinoline-1-carboxylate hemifumarate.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 1 M hydrochloric acid, water
  3. concentrationa 1 M aqueous sodium hydroxide solution, and saturated brine, and concentrated
  4. customthe residue was purified by silica gel column chromatography (elution solvent: HEX-EtOAc)
  5. dissolutionThe resulting substance was dissolved in chloroform
  6. additionby adding 0.05 ml of trifluoroacetic acid
  7. stirringstirring for 30 minutes
  8. concentrationAfter concentration under reduced pressure
  9. dissolutionthe resultant was dissolved in EtOH
  10. additionneutralized by the addition of triethylamine
  11. concentrationconcentrated under reduced pressure
  12. customThen, the residue was purified by silica gel column chromatography (elution solvent: chloroform-MeOH-aqueous ammonia)
  13. dissolutionThe resulting substance was dissolved in EtOH
  14. addition76 mg of fumaric acid was added
  15. filtrationThe resulting white solid was collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-3bfc27dfb65640e4b918904bcbae0982
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

Loading…