Dichloromethane → ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate

HRID 39780Notes

Reaction equation

HRID 39780 reaction equation
ClCCl.C(OC([N:11]([CH2:40][C:41]1[CH:50]=[CH:49][C:44]2[O:45][CH2:46][CH2:47][O:48][C:43]=2[CH:42]=1)[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][N:20]2[C:29]3[C:24](=[C:25](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=3)[CH:23]=[CH:22][C:21]2=[O:39])[CH2:14][CH2:13]1)=O)(C)(C)C.FC(F)(F)C(O)=O>CCCCCC>[O:45]1[C:44]2[CH:49]=[CH:50][C:41]([CH2:40][NH:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][N:20]4[C:29]5[C:24](=[C:25](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=5)[CH:23]=[CH:22][C:21]4=[O:39])[CH2:16][CH2:17]3)=[CH:42][C:43]=2[O:48][CH2:47][CH2:46]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68193064HCID 68193064, compound

Product 1

HCID 86643185ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylateYield 94.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 3 mL of a dichloromethane solution containing 0.15 g of ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate, 3 mL of trifluoroacetic acid was added and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 10 with 20% aqueous sodium hydroxide solution, under ice-cooling. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, hexane was added and the resulting solid was filtered to give 0.12 g of ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate as a light brown solid.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, chloroform and water
  3. additionwere added
  4. temperaturecooling
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washwashed sequentially with water and aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customTo the residue thus obtained
  11. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-c11730601c4744948fe7a28e382d88c2
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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