4-Nitrobenzoic Acid → HCID 59175908, compound

HRID 1807704Notes

Reaction equation

HRID 1807704 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(#N)C>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][C:8]3[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])[CH2:2][CH2:3]2)=[O:26])=[CH:28][CH:29]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28325078Methyl 3-[(piperazin-1-yl)methyl]benzoate

Product 1

HCID 59175908HCID 59175908, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-(piperazin-1-ylmethyl)benzoate (2.47 g, 10.542 mmol), 4-nitrobenzoic acid (1.77 g, 10.542 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.03 g, 15.813 mmol), triethylamine (2.94 mL, 21.084 mmol) and acetonitrile (40 mL) were stirred together, at ambient temperature, for 4 hours before being concentrated under vacuum. The residue was dissolved in ethyl acetate, filtered, washed with water (×2) and treated with strong cation exchange column chromatography to afford the title compound (3.12 g). MS (ESI) m/z 384.3 [M+H]+

Workup

  1. concentrationbefore being concentrated under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. filtrationfiltered
  4. washwashed with water (×2)
  5. additiontreated with strong cation exchange column chromatography

Sources & evidence

ORD record
ord-57ef3320ce81475a96b301ca3cca24f7
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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