Ethanol → HCID 22272508, compound

HRID 230470Notes

Reaction equation

HRID 230470 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2].CCO.O.NN>CCO.C1COCC1.[Ni]>[NH2:10][C:9]1[CH:8]=[CH:7][C:6]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]2)=[CH:5][C:4]=1[NH:3][CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 22272427HCID 22272427, compound

Product 1

HCID 22272508HCID 22272508, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of tert-butyl 4-[3-(ethylamino)-4-nitrophenyl]-1-piperazinecarboxylate (1.028 g, 2.93 mmol) in 40 mL EtOH:THF (4:1) solvent system was added Raney-Ni (1 mL of a EtOH suspension) followed by addition hydrazine hydrate (0.734 g, 14.67 mmol). The mixture was stirred vigorously for 3 hours and then; filtered through a Celite pad pretreated with water. The filtrate was concentrated and then purified by column chromatography on silica using CHCl3/MeOH/NH3 9:1:0.4% as eluent to give 0.877 g (93%) of a red oil. The oil was used immediately in the next reaction. HPLC purity >90%; MS (posEI) m/z=320 (M+);

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-61af6f37051d4046b8c0be19a0321e26
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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