Potassium Carbonate → HCID 22485267, compound

HRID 353384

Reaction equation

HRID 353384 reaction equation
Cl.COC1C=C(C=CC=1OC)OC1C=CC(S([C:17]2(C(NO)=O)CC[N:20](CC#C)[CH2:19][CH2:18]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].CO[C:43]1[CH:44]=[C:45](O)[CH:46]=[CH:47][C:48]=1[O:49]C>CN(C)C=O>[O:49]([NH:20][CH2:19][C:18]#[CH:17])[C:48]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162513,4-DimethoxyphenolHCID 1317238364-[[4-(3,4-dimethoxyphenoxy)phenyl] sulfonyl]-N-hydroxy-1-(2-propynyl)-4-piperidinecarboxamide, monohydrochloride

Product 1

HCID 22485267HCID 22485267, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part C: To a solution of the propargyl amine of part B (8 g, 22.63 mmol) and powdered K2CO3 (8.8 g, 56.6 mmol) in N,N-dimethylformamide (150 mL) was added 3,4-dimethoxyphenol (6.98 g, 45 mmol) at ambient temperature. The composition was heated to 90 degrees Celsius for 36 hours. The solution was concentrated under high vacuum and the residue was dissolved in ethyl acetate. The organic layer was washed with 1N NaOH, H2O and dried over MgSO4. Chromatography (on silica, ethyl acetate/hexane) provided phenoxy propargyl amine as light yellow gel (10 g, 90.9%).

Workup

  1. temperatureThe composition was heated to 90 degrees Celsius for 36 hours
  2. concentrationThe solution was concentrated under high vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with 1N NaOH, H2O
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-c4f247054abc48ff84edbe21d6b3c677
Source dataset
uspto-grants-2004_06
Patent number
US06750233B2

Linked notes

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