HCID 66815552, compound → HCID 59859896, compound

HRID 1944536Notes

Reaction equation

HRID 1944536 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 66815552HCID 66815552, compound

Product 1

HCID 59859896HCID 59859896, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(4-azepan-1-yl-phenyl)-acrylic acid ethyl ester (1.0 g, 3.65 mmol) in ethanol (20 Ml) was hydrogenated at 55 psi over 10% palladium (0.1 g) for 18 hours. The catalyst was removed by filtration, and the solvent was evaporated in vacuo. The crude product was purified by flash silica gel chromatography, using 5% ethyl acetate in hexane as the eluant, to give the product, 1.0 g (99%), a color less oil. MS: m/z 276 (MH+). 1H NMR (CDCl3): 1.24 (t, 3 H), 1.48-1.61 (m, 4 H), 1.76 (m, 4 H), 2.56 (t, 2 H), 2.84 (t, 2 H), 3.42 (t, 4 H), 4.13 (q, 2 H), 6.61 (d, 2 H) and 7.03 (d, 2 H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated in vacuo
  3. customThe crude product was purified by flash silica gel chromatography
  4. customto give the product, 1.0 g (99%)

Sources & evidence

ORD record
ord-61d5f831e170486fbd221f087e59ac07
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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