Hydrogen chloride-ethyl acetate → HCID 67539389, compound

HRID 2193239Notes

Reaction equation

HRID 2193239 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([CH2:40][OH:41])[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:42])[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[ClH:43].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:43].[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([CH2:40][OH:41])[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:42])[CH2:22][CH2:21]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 59397958HCID 59397958, compound

Product 1

HCID 67539389HCID 67539389, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 10 mL of an ethyl acetate solution containing 220 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-hydroxymethyl-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 5 mL of 4 mol/L hydrogen chloride/ethyl acetate was added and stirred at room temperature. The resulting solid was filtered, 5 mL of 4 mol/L hydrochloric acid was added and stirred at room temperature. To the reaction mixture, methanol was added, and the solvent was removed under reduced pressure to give 118 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-5-hydroxymethyl-7-methoxyquinolin-2(1H)-one hydrochloride as a pale yellow solid.

Workup

  1. additionwas added
  2. filtrationThe resulting solid was filtered
  3. addition5 mL of 4 mol/L hydrochloric acid was added
  4. stirringstirred at room temperature
  5. additionTo the reaction mixture, methanol was added
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7e8703e8ea1c4f6ab379ece7121c1a93
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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