Acetic Acid → 1-Methyl-4-(4-nitrobenzyl)piperazine

HRID 1262007Notes

Reaction equation

HRID 1262007 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[C:18](O)(=O)C.C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>>[CH3:18][N:12]1[CH2:17][CH2:16][N:15]([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 6

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 4837PiperazineHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 6777951-Methyl-4-(4-nitrobenzyl)piperazine

Procedure

p-Nitrobenzaldehyde (2.50 g, 16.5 mmol) and piperazine, 1-methyl- (3.31 g, 33.1 mmol) were dissolved in Acetic acid (2.0 mL, 35 mmol) and Methylene chloride (100 mL, 2000 mmol) and the solution was allowed to stir at room temperature for approximately 15 minutes. Sodium triacetoxyborohydride (5.26 g, 24.8 mmol) was then added and the reaction was allowed to stir overnight. The reaction mixture was poured over saturated sodium bicarbonate and organics were extracted with dichloromethane. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent). Combined fractions were reduced and dried under vacuum to afford 3.77 g of 1-Methyl-4-(4-nitro-benzyl)-piperazine. (M+H)=236.6.

Workup

  1. stirringto stir overnight
  2. extractionorganics were extracted with dichloromethane
  3. dry with materialCombined extracts were then dried over sodium sulfate
  4. filtrationfiltered
  5. customThe crude reaction mixture
  6. customwas then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f1f7cf9dfa0047ee94206c779ed81474
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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