Hydrazine → 2-(4-(4-Ethylbenzyl)piperazin-1-yl)acetohydrazide

HRID 1406671Notes

Reaction equation

HRID 1406671 reaction equation
[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15](OCC)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)=[CH2:2].[NH2:22][NH2:23]>C(O)C>[CH2:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:22][NH2:23])=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681371HCID 86681371, compound

Product 1

HCID 866813722-(4-(4-Ethylbenzyl)piperazin-1-yl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 9 (3.23 g, 11.2 mmol, 1 equiv.), anhydrous hydrazine (1.1 mL, 33.6 mmol, 3 equiv.), ethanol (22.6 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{28} (1.92 g, 62%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 8.14 (br s, 1H), 7.20 (d, 2H, J=8.0 Hz), 7.14 (d, 2H, J=8.0 Hz), 3.84 (d, 2H, J=4.0 Hz), 3.47 (s, 2H), 3.06 (s, 2H), 2.63 (q, 2H, J=7.5 Hz), 2.53 (br s, 4H), 2.45 (br s, 4H), 1.22 (t, 3H, J=7.5 Hz). 13C-NMR (125 MHz, CDCl3): δ 170.5, 143.1, 134.9, 129.1, 127.7, 62.6, 60.5, 53.6, 52.9, 28.5, 15.5.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{28} (1.92 g, 62%) as a white solid

Sources & evidence

ORD record
ord-6a848daab7714414b0a881d6ee10aa7b
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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