Hydrochloric Acid → HCID 19025748, compound

HRID 1464400Notes

Reaction equation

HRID 1464400 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH:2]([CH3:4])[CH3:3].[CH:28]1(Br)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl>CN(C=O)C>[CH2:1]([C:5]1[CH:6]=[C:7]([CH:23]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:24]([O:26][CH3:27])=[O:25])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7960Cyclohexyl bromideHCID 19087768HCID 19087768, compound

Product 1

HCID 19025748HCID 19025748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

12 g (0.003 mol) of methyl 2-[3-isobutyl-4-(quinolin-2-yl-methoxy)phenyl]acetate and 6.52 g (0.04 mol)=4.9 ml of cyclohexyl bromide are dissolved in 36 ml of DMF under an argon atmosphere and the solution is cooled to 0° C. 4.88 g (0.04 mol) of potassium tertiary butylate, dissolved in 80 ml of DMF, are added dropwise thereto with stirring. After a reaction time of about 2 hours the temperature is allowed to rise to RT and the mixture is acidified with 2N hydrochloric acid and evaporated to dryness in vacuo. The remaining residue is extracted with 100 ml of dichloromethane and 50 ml of water, the organic phase is separated off, dried with Na2SO4, evaporated to a small volume in vacuo and the remaining residue is separated by column chromatography (silica gel 60, mobile solvent: dichloromethane/ethyl acetate=100/2).

Workup

  1. additionare added dropwise
  2. customAfter a reaction time of about 2 hours
  3. customto rise to RT
  4. customevaporated to dryness in vacuo
  5. extractionThe remaining residue is extracted with 100 ml of dichloromethane and 50 ml of water
  6. customthe organic phase is separated off
  7. dry with materialdried with Na2SO4
  8. customevaporated to a small volume in vacuo
  9. customthe remaining residue is separated by column chromatography (silica gel 60, mobile solvent: dichloromethane/ethyl acetate=100/2)

Sources & evidence

ORD record
ord-ca13aa758fdc4c519d34040a23edd010
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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