4-Hydroxy-3-nitrobenzaldehyde → HCID 21263910, compound

HRID 566876Notes

Reaction equation

HRID 566876 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[N+:24]([O-:26])=[O:25].C[C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1>C1COCC1>[CH3:1][C:30]1[CH:29]=[CH:28][CH:33]=[CH:32][C:31]=1[N:34]1[CH2:35][CH2:36][N:37]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([OH:15])=[C:17]([N+:24]([O-:26])=[O:25])[CH:18]=2)[CH2:38][CH2:39]1

Participants

5

Reactant 3

HCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 831131-(p-Tolyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21263910HCID 21263910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (1.8 g, 8.4 mmol) is added to a solution of 4-hydroxy-3-nitro-benzaldehyde (1.3 g, 8.0 mmol) and 1-(4-methyl-phenyl)-piperazine (2.8 g, 16.1 mmol) in 50 mL of THF at room temperature, and the mixture is stirred overnight. The reaction is quenched by pouring into 400 mL of water, and the precipitate which forms is collected by filtration. Yield=1.7 g (33%) of 4-[4-(methylphenyl)-piperazin-1-ylmethyl]-2-nitro-phenol oil.

Workup

  1. customThe reaction is quenched
  2. additionby pouring into 400 mL of water
  3. filtrationthe precipitate which forms is collected by filtration

Sources & evidence

ORD record
ord-04c6d355948c4d199f83dc05e1f12a69
Source dataset
uspto-grants-2001_01
Patent number
US06177422B1

Reaction notes

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