Triethylamine → HCID 66671056, compound

HRID 591813Notes

Reaction equation

HRID 591813 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH2:10][N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)[CH:7]=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 13399988Methyl 5-(bromomethyl)-2-nitrobenzoate

Product 1

HCID 66671056HCID 66671056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-bromomethyl-2-nitrobenzoic acid methyl ester (3.00 g, 10.9 mmol) in CH2Cl2 (100 mL) was added triethylamine (3.30 g, 33.0 mmol) and 1-methylpiperazine (3.30 g, 33.0 mmol). The mixture was heated at 50° C. under nitrogen for 16 hours, then concentrated to give crude 5-(4-methylpiperazin-1-ylmethyl)-2-nitrobenzoic acid methyl ester, which was purified by column chromatography (silica gel 230-400 mesh; 1-5% methanol in dichloromethane as eluent). Yield: 3.0 g (93%). It was further converted to its hydrochloride salt (3.7 g) by stirring in 1 M HCl in ether and was isolated by filtration.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-a6243f6d7d044514b84f3762d4d577a7
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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