Dichloromethane → HCID 59398294, compound

HRID 39806Notes

Reaction equation

HRID 39806 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-2367bb33fcc64c95acb25489ed4bfe4d
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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