Hydrochloric Acid → HCID 131724535, compound

HRID 1836572Notes

Reaction equation

HRID 1836572 reaction equation
C([N:8]1[CH2:20][C@H:19]2[C@:10](C(OCC)=O)([C:11](=O)[N:12]3[CH2:23][CH2:22][CH2:21][C:14]4[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]3=4)[CH2:9]1)C1C=CC=CC=1.[ClH:30]>O1CCOCC1>[ClH:30].[ClH:30].[CH:17]1[CH:16]=[CH:15][C:14]2[CH2:21][CH2:22][CH2:23][N:12]3[C:13]=2[C:18]=1[C@@H:19]1[CH2:20][NH:8][CH2:9][C@@H:10]1[CH2:11]3

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131724536HCID 131724536, compound

Product 1

HCID 131724535HCID 131724535, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (±)-cis ethyl 10-benzyl-8-oxo-5,6,9,10,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-8a(8H)-carboxylate (36.6 g, 93.7 mmol) in 400 mL of 1,4-dioxane was added 400 mL of 3M HCl and the resulting mixture was stirred at 100° C. for 24 h. The dioxane and most of the water was removed in vacuo, and the residue was basified with 1N NaOH and extracted with ethyl acetate. The layers were separated and the organics were washed with brine, dried (MgSO4) and concentrated to afford 28.0 g (94%) of the title compound of Part C, which was sufficiently pure to be used without purification. 1H NMR (CDCl3) δ: 7.25-7.15 (m, 5H), 6.93-6.78 (m, 3H), 4.02-3.93 (m, 1H), 3.78-3.66 (m, 1H), 3.63 (8, 2H), 3.55-3.45 (m, 1H), 3.35 (dd, 1H, J=9.7, 8.3 Hz), 3.20-3.07 (m, 2H), 2.96 (dd, 1H, J=9.5, 5.1 Hz), 2.75-2.68 (m, 2H), 2.32 (app t, 1H, J=9.4 Hz), 1.92-1.82 (m, 2H).

Workup

  1. customThe dioxane and most of the water was removed in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe layers were separated
  4. washthe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b9329e2f01c46bfbd46d1ec676cf68d
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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