Potassium Carbonate → HCID 22923676, compound

HRID 2257907Notes

Reaction equation

HRID 2257907 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-cyclo-octylmethyl-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-5623de3644f548f8b6eb603c27c20eca
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

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