Methyl Acrylate → HCID 59769453, compound

HRID 32183Notes

Reaction equation

HRID 32183 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>O1CCCC1>[CH3:28][O:27][C:23](=[O:26])[CH2:24][CH2:25][N:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:8]2[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 23143039HCID 23143039, compound

Product 1

HCID 59769453HCID 59769453, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of 1-[2-(4-t-butylcyclohexyl)phenyl]piperazine (530 mg, 1.76 mmol) produced in Example (10a) and tetrahydrofuran (2 mL) was added methyl acrylate (0.24 mL, 2.65 mmol), followed by stirring for 12 hours at an external temperature of 45° C. The reaction mixture was concentrated under reduced pressure and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 643 mg of the title compound as colorless crystals, as a mixture of diastereomers at the position of t-butylcyclohexyl.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-55a9d64e6f624540bcb930ff0bf222d7
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

Loading…