Potassium Carbonate → HCID 21873326, compound

HRID 723344Notes

Reaction equation

HRID 723344 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH:13][CH2:17][CH:16]([O:19][CH3:20])[O:15][CH3:14])=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 64844484-(cyclopentyloxy)aniline

Product 1

HCID 21873326HCID 21873326, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-cyclopentyloxyphenylamine (8.86 g), bromo-acetaldehyde dimethyl acetal (12.2 g), potassium carbonate (13.8 g) and dimethylformamide (100 ml) was heated at 100° C. for 5 hours. Cooling was followed by filtration and concentration of the filtrate. The residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 4:1). The product with the molecular weight of 265.36 (C15H23NO3); MS (ESI): 266 ([M+H]+), was obtained in this way.

Workup

  1. temperatureCooling
  2. filtrationwas followed by filtration and concentration of the filtrate
  3. customThe residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 4:1)
  4. customMS (ESI): 266 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-2a391724a42944499169b84713ce0b2b
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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