Oxalyl chloride → 4-(4-methylpiperazin-1-yl)benzoyl Chloride

HRID 1361649Notes

Reaction equation

HRID 1361649 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(Cl)(=O)C([Cl:20])=O>ClCCl.CN(C)C=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([Cl:20])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 7365324-(4-Methylpiperazin-1-yl)benzoic acid

Product 1

HCID 116300684-(4-methylpiperazin-1-yl)benzoyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round bottom flask, dissolved 4-(4-methylpiperazin-1-yl)benzoic acid (1.00 g, 4.50 mmol) in dichloromethane (5.0 mL). Added oxalyl chloride (1.2 mL, 9.1 mmol) and N,N-dimethylformamide (2 drops). Stirred at RT for 2 hours. Concentrated and isolated 4-(4-methylpiperazin-1-yl)benzoyl chloride as an off-white solid. LC/MS of methyl ester (quenched with methanol) revealed an MS (M+H)+ of 235; Calc'd 234.29 for C13H18N2O2 (methyl ester).

Workup

  1. concentrationConcentrated

Sources & evidence

ORD record
ord-ef80cc0e9b39412388603f71854dc180
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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