Hydrochloric Acid → HCID 68993634, compound

HRID 656916Notes

Reaction equation

HRID 656916 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[O:12][CH2:13][CH2:14][O:15][C:5]=3[C:4]=2[N:3]1[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20][CH2:19]1.Cl>C(Cl)(Cl)Cl.O1CCOCC1.CO>[NH2:24][CH:21]1[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][N:3]2[C:4]3[C:5]4[O:15][CH2:14][CH2:13][O:12][C:6]=4[CH:7]=[CH:8][C:9]=3[CH:10]=[CH:11][C:2]2=[O:1])[CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86635316HCID 86635316, compound

Product 1

HCID 68993634HCID 68993634, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl {1-[2-(9-oxo-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10(9H)-yl)ethyl]-4-piperidinyl}carbamate (1 g; 2.34 mmol) was dissolved in chloroform (8 ml) and 4M HCl in 1,4-dioxane (10 ml) added. This was then stirred at rt for 1 h. The salts from the reaction were dissolved in MeOH and all solvents then removed. The residues were redissolved in MeOH and stirred with amberlyst ion exchange resin until a neutral pH was reached. The resin was filtered off and all solvents were removed. The crude residues were subjected to column chromatography on silica gel using a 0-20% 2M NH3: MeOH/DCM gradient to give the desired product (425 mg; 55%).

Workup

  1. customall solvents then removed
  2. dissolutionThe residues were redissolved in MeOH
  3. stirringstirred with amberlyst ion exchange resin until a neutral pH
  4. filtrationThe resin was filtered off
  5. customall solvents were removed

Sources & evidence

ORD record
ord-56671d95d422426fa61f776e04f7c6ca
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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