Dichloromethane → HCID 59398294, compound

HRID 2193178Notes

Reaction equation

HRID 2193178 reaction equation
ClCCl.[O:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH:17]3[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([CH3:43])=[CH:34][C:35](=[O:42])[N:36]2[CH2:39][CH:40]=O)=[CH:31][CH:30]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.C(Cl)(Cl)Cl.C(O)(=O)C>[O:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH2:40][CH2:39][N:36]4[C:37]5[C:32](=[CH:31][CH:30]=[C:29]([O:28][CH3:27])[CH:38]=5)[C:33]([CH3:43])=[CH:34][C:35]4=[O:42])[CH2:18][CH:17]3[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59397837(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehydeHCID 59398324HCID 59398324, compound

Product 1

HCID 59398294HCID 59398294, compoundYield 64.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 2.5 mL of dichloromethane solution containing 0.14 g of ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)piperazine-2-carboxylate and 0.10 g of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 25 μL of acetic acid were added and stirred at room temperature for 50 min. Then, 0.14 g of sodium triacetoxyborohydride was added, and stirred at room temperature for 1 hour. To the reaction mixture, chloroform and water were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:acetone=50 1], to give 0.15 g of ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate as a colorless foam.

Workup

  1. additionwere added
  2. stirringstirred at room temperature for 1 hour
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; chloroform:acetone=50 1]

Sources & evidence

ORD record
ord-64a8976538584820b2d1043a5befe114
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

Loading…