Tetrahydrofuran → N-(4-aminobenzyl)-N-(2-pyridinyl)amine

HRID 1388078Notes

Reaction equation

HRID 1388078 reaction equation
C1COCC1.[BH4-].[Na+].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:13][CH:12]=1)([O-])=O>CO.[Ni](Br)Br>[NH2:8][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydride3×HCID 184725022-[(4-Nitrophenyl)methylamino]pyridine

Product 1

HCID 11788863N-(4-aminobenzyl)-N-(2-pyridinyl)amineYield 46.1%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of nickel bromide (44 mg) in methanol (4 ml)/THF (4 ml) was added sodium boro hydride (40 mg), and the mixture was stirred. To the mixture was added 2-[(4-nitrophenyl)methylamino]pyridine (0.92 g) and then sodium boro hydride (414 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added nickel bromide (44 mg) and sodium boro hydride (454 mg), and the mixture was stirred at room temperature for 2 hours. Insoluble materials were filtered off with sellaite, and to the filtrate was added sodium bicarbonate solution. The mixture was extracted with ethyl acetate and washed with brine. The extract was dried (anhydrous magnesium sulfate) and concentrated, and the residue was purified twice with silica gel column chromatography (ethyl acetate/hexane=1/1) to give 2-[(4-aminophenyl)methylamino]pyridine (369 mg) as pale red solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. filtrationInsoluble materials were filtered off with sellaite
  3. additionto the filtrate was added sodium bicarbonate solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe extract was dried (anhydrous magnesium sulfate)
  7. concentrationconcentrated
  8. customthe residue was purified twice with silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-9a771f31a8544f95b0c383a4c87596ba
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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