2,4-Dimethoxybenzoyl chloride → HCID 17987580, compound

HRID 1982932Notes

Reaction equation

HRID 1982932 reaction equation
Cl.[CH2:2]=[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:9][O:10][C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>ClCCl>[CH3:9][O:10][C:11]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:12]=1[C:13]([N:6]1[CH2:7][CH2:8][C:3](=[CH2:2])[CH2:4][CH2:5]1)=[O:14]

Participants

4

Reactant 2

HCID 27347192,4-Dimethoxybenzoyl chlorideHCID 226658264-Methylidenepiperidine--hydrogen chloride (1/1)

Product 1

HCID 17987580HCID 17987580, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-methylene-piperidine hydrochloride (1.00 g, 8.12 mmol, JOC 66,2487-2492,2001) in 10 mL anhydrous dichloromethane at room temperature is added 2,4-dimethoxybenzoyl chloride (1.63 g, 8.12 mmol) and TEA (4 g, 40 mmol). The reaction mixture is allowed to stir for 16 hours. Dichloromethane is removed in vacuo, and the resultant residue is purified through silica gel chromatography (95% DCM, 5% MeOH) to give (2,4-dimethoxy-phenyl)-(4-methylene-piperidin-1-yl)-methanone. Yield: 1.62 g, 6.23 mmol. m/z (MS) M+1 261.01.

Workup

  1. customDichloromethane is removed in vacuo
  2. customthe resultant residue is purified through silica gel chromatography (95% DCM, 5% MeOH)

Sources & evidence

ORD record
ord-4b69278aa7ab45dd8a33fc9591f305df
Source dataset
uspto-grants-2009_06
Patent number
US07541368B2

Reaction notes

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