Hydrochloric Acid → HCID 131724527, compound

HRID 1836561Notes

Reaction equation

HRID 1836561 reaction equation
Cl.C([N:9]1[CH2:21][C@@H:20]2[C@H:11]([C:12](=[O:25])[N:13]3[CH2:24][CH2:23][CH2:22][C:15]4[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]3=4)[CH2:10]1)C1C=CC=CC=1.[Cl:26]C(OC(Cl)C)=O.C(=O)([O-])[O-].[Na+].[Na+].Cl.CCOCC>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[ClH:26].[CH:18]1[CH:17]=[CH:16][C:15]2[CH2:22][CH2:23][CH2:24][N:13]3[C:14]=2[C:19]=1[C@@H:20]1[CH2:21][NH:9][CH2:10][C@H:11]1[C:12]3=[O:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 131724526HCID 131724526, compound

Product 1

HCID 131724527HCID 131724527, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (±)-trans-10-benzyl-5,6,9,10,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinolin-8(8aH)-one from EXAMPLE 1, Part E (1.2 g, 3.8 mmol) in 20 mL of toluene was added 1-chloroethyl chloroformate (0.81 mL, 7.53 mmol) and the resulting solution was stirred at 110° C. for 3 h. The reaction mixture was cooled and the toluene was removed under reduced pressure. The residue was taken up in 20 mL of methanol and was stirred at 65° C. for 1 h. The reaction was cooled and the methanol was removed under reduced pressure. A portion of the residue (50 mg, 0.19 mol) was partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo. The residue was dissolved in ether and there was added 2M HCl in ether (0.095 mL, 0.19 mmol). The solvent was decanted and the remaining solid was triturated twice with ether and was dried in vacuo to afford 25 mg (50%) of the title compound of EXAMPLE 3 as an off white powder. LRMS (ES)+: 270.3 (M+H+CH3CN)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe toluene was removed under reduced pressure
  3. stirringwas stirred at 65° C. for 1 h
  4. temperatureThe reaction was cooled
  5. customthe methanol was removed under reduced pressure
  6. washThe organics were washed with brine
  7. dry with materialdried (K2CO3)
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in ether
  10. customThe solvent was decanted
  11. customthe remaining solid was triturated twice with ether
  12. customwas dried in vacuo

Sources & evidence

ORD record
ord-ac636a3b306f4d908534fad3f87ad007
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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