Tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate → N-Ethyl-3-methyl-4-(piperazin-1-yl)benzamide

HRID 1184462Notes

Reaction equation

HRID 1184462 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]>Cl.O1CCOCC1.C(OCC)C>[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 1

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

Product 1

HCID 28749600N-Ethyl-3-methyl-4-(piperazin-1-yl)benzamideYield 99%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate 296 (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 the title compound as a white solid (0.7528 g, 2.65 mmol, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.20 Hz, 3H) 2.29 (s, 3H) 3.00-3.14 (m, 4H) 3.16-3.32 (m, 6H) 7.07 (d, J=8.34 Hz, 1H) 7.62-7.71 (m, 2H) 8.34 (t, J=5.43 Hz, 1H) 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-355d19c7ded541ca897653993912af91
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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