Potassium Carbonate → HCID 9955530, compound

HRID 1107398Notes

Reaction equation

HRID 1107398 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:24])[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Cl)=[CH:35][CH:34]=1>O1CCOCC1.O>[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:24])[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:10]([CH3:12])[CH3:11])[CH2:5][CH2:6]2)=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 9949483HCID 9949483, compound

Product 1

HCID 9955530HCID 9955530, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

N-(4-Piperidinyl)-2-butoxy-3-methyl-2-phenylbutanamide (invention compound, Compound No. 27) (4.5 g) was dissolved in dioxane (25 ml) and water (25 ml). To the resulting solution, potassium carbonate (0.7 g) and 4-methoxybenzyl chloride (0.8 g) were added, followed by stirring at room temperature for 2 days. To the reaction mixture, was added water (40 ml). The resulting mixture was extracted with an ethyl acetate. The extract was then dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by a silica gel column to obtain the invention compound (Compound No. 29, 0.60 g, 26.4%) as a colorless oil.

Workup

  1. extractionThe resulting mixture was extracted with an ethyl acetate
  2. dry with materialThe extract was then dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by a silica gel column
  5. customto obtain the invention compound (Compound No. 29, 0.60 g, 26.4%) as a colorless oil

Sources & evidence

ORD record
ord-2e2b195fe7a74548bcf643aa10e1c64d
Source dataset
uspto-grants-2000_05
Patent number
US06060485

Reaction notes

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