Piperidine → HCID 68537123, compound

HRID 1931408Notes

Reaction equation

HRID 1931408 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C([O:11][C:12](=O)[CH2:13][C:14]([CH3:31])([C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:19][CH:20]=1)[CH3:15])C>CN(C=O)C>[CH3:31][C:14]([C:16]1[N:17]=[C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=2)[S:19][CH:20]=1)([CH3:15])[CH2:13][C:12]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 24758Sodium hydrideHCID 68537700HCID 68537700, compound

Product 1

HCID 68537123HCID 68537123, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

27.5 mg (0.63 mmol) of sodium hydride (55% in mineral oil) were added to 53.6 mg (0.63 mmol) of piperidine in 2 ml of DMF. After stirring at room temperature for 30 min, 150 mg (0.42 mmol) of 3-methyl-3-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-butyric acid ethyl ester in 2 ml of DMF were added, and the reaction mixture was stirred at room temperature for 2 h. After evaporation, water and dichloromethane were added, the organic phase was separated, washed with water, dried, and evaporated. The product was purified by RP18 chromatography. Yield: 6.3 mg.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. customAfter evaporation, water and dichloromethane
  3. additionwere added
  4. customthe organic phase was separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customThe product was purified by RP18 chromatography

Sources & evidence

ORD record
ord-1906d63586d14b4c88ae3b122a0329d3
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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