Potassium Carbonate → HCID 15677012, compound

HRID 1090708Notes

Reaction equation

HRID 1090708 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:23])[NH:10]2.[NH:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:37])[O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].[Br-].[Li+]>CN(C)C=O>[C:17]1([CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:24]3[CH2:25][CH2:26][CH:27]([NH:30][C:31]([O:32][CH2:33][CH:34]4[CH2:35][CH2:36]4)=[O:37])[CH2:28][CH2:29]3)=[C:6]3[C:11]=2[NH:10][C:9](=[O:23])[CH2:8][CH2:7]3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 82050Lithium BromideHCID 15676967HCID 15676967, compoundHCID 15676998HCID 15676998, compound

Product 1

HCID 15677012HCID 15677012, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-(2-chloroethoxy)-8-phenylmethoxy-3,4-dihydrocarbostyril (0.7 g), from Preparation 6, and cyclopropylmethyl 4-piperidylcarbamate (0.5 g) were dissolved in dimethylformamide (35 mL) containing potassium carbonate (0.3 g) and lithium bromide (0.3 g). The reaction medium was heated for 34 hours at 110° C., and the solvent was then removed by evaporation under reduced pressure. The residue was dissolved in chloroform (70 mL), and the solution was washed with water (2×40 mL), dried over sodium sulfate, and the solvent was evaporated under reduced pressure. Flash chromatography of the residue, using dichloromethane/methanol (90:10) as eluent, afforded 1 g of the title compound 8-phenylmethoxy-3,4-dihydro-5-[2-(4-((cyclopropylmethoxy)carbonylamino)-1-piperidyl)ethoxy]carbostyril as a yellow oil (ca. 95%).

Workup

  1. customthe solvent was then removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform (70 mL)
  3. washthe solution was washed with water (2×40 mL)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-397b2f2398494b42aa3af2c9d7a2894a
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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