Sodium hydride → HCID 68453840, compound

HRID 2358399Notes

Reaction equation

HRID 2358399 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:8]=1[OH:17])[CH3:2].[H-].[Na+].Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:9][C:8]=1[O:17][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 68457399HCID 68457399, compound

Product 1

HCID 68453840HCID 68453840, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-tert-Butyl-2-hydroxyphenyl)acrylic acid ethyl ester (59.0 mg, 0.238 mmol) and NaH (47.5 mg, 60% disp. oil, 5 eq) were added in anhydrous DMF. The reaction mixture was cooled down to 0° C. 1-(2-Chloroethyl)piperidine hydrochloride (87.6 mg 0.476 mmol, 2 eq) was added. The mixture was heated to 90° C. The reaction was stirred for 12 hr at 90° C. The reaction was quenched by adding H2O. The reaction mixture extracted with EtOAc and then washed with H2O and brine. The residue was purified with column chromatography (EtOAc) to give a yellow liquid (14.0 mg, 16.4%).

Workup

  1. temperatureThe mixture was heated to 90° C
  2. customThe reaction was quenched
  3. additionby adding H2O
  4. extractionThe reaction mixture extracted with EtOAc
  5. washwashed with H2O and brine
  6. customThe residue was purified with column chromatography (EtOAc)

Sources & evidence

ORD record
ord-4f12423ad259462e8e87e3aae007fce1
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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