Potassium Carbonate → HCID 22923676, compound

HRID 1720311Notes

Reaction equation

HRID 1720311 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH3:19][O:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][N:31]([CH2:35][CH2:36][CH2:37]Cl)[C:32]([NH2:34])=[O:33])[CH2:25][CH2:24]1>CN(C)C=O>[CH3:19][O:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][N:31]([C:32]([NH:34][CH2:5][CH2:6][CH2:7][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)=[O:33])[CH2:35][CH:36]2[CH2:37][CH2:9][CH2:10][CH2:11][CH2:2][CH2:3][CH2:4]2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 131719373HCID 131719373, compound

Product 1

HCID 22923676HCID 22923676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.6 g of 6-hydroxycarbostyril, 1.4 g of potasium carbonate and 4.2 g of N-cyclooctylmethyl-N-[2-(4-methoxymethoxy-1-piperidinyl)-ethyl-N-(3-chloropropyl)urea in 20 ml of dimethylformamide was stirred at 80° C. for 1 day. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The extract was washed with water and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was purified by a silica gel column chromatography (eluant: 5% methanol/dichloromethane) to obtain 0.76 g of 6-[3-{N-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]-N-cyclooctylmethylamino}carbonylaminopropoxy]carbostyril.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe resulting residue was purified by a silica gel column chromatography (eluant: 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-13e4a23590364186b1ce1ff87f6206b3
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

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