Hydrochloric Acid → N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide hydrochloride

HRID 2097907Notes

Reaction equation

HRID 2097907 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[C:8]([CH3:25])[CH:7]=1)=[O:5])[CH3:2].[ClH:26]>O1CCOCC1.C(OCC)C>[ClH:26].[CH2:1]([NH:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[C:8]([CH3:25])[CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58324366Tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate

Product 1

HCID 66775291N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate (0.9323 g, 2.68 mmol) was diluted with 4.0M HCl in dioxane (8 mL) and stirred for 30 min. The thick white precipitate that formed was diluted with ethyl ether (10 mL) and stirred until a fine suspension resulted. The precipitate was filtered under nitrogen, washed with ether (5 mL) and dried in vacuum to afford N-ethyl-3-methyl-4-(piperazin-1-yl)benzamide hydrochloride (0.7528 g, 2.65 mmol, 99% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.20 Hz, 3 H) 2.29 (s, 3 H) 3.00-3.14 (m, 4 H) 3.16-3.32 (m, 6 H) 7.07 (d, J=8.34 Hz, 1 H) 7.62-7.71 (m, 2 H) 8.34 (t, J=5.43 Hz, 1 H) 9.17 (br. s., 2 H). ESI-MS: m/z 248.2 (M+H)+.

Workup

  1. customThe thick white precipitate that formed
  2. stirringstirred until a fine suspension
  3. customresulted
  4. filtrationThe precipitate was filtered under nitrogen
  5. washwashed with ether (5 mL)
  6. customdried in vacuum

Sources & evidence

ORD record
ord-5a8d774358eb42d988b8d8c2cf69de26
Source dataset
uspto-grants-2013_05
Patent number
US08450323B2

Reaction notes

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