Sodium borohydride → 6-Methyl-N4-(2-methylpropyl)-N2, N2-bis(phenylmethyl)pyridine-2,3,4-triamine

HRID 1757576Notes

Reaction equation

HRID 1757576 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]([N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([N+:25]([O-])=O)=[C:6]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:5]=1>CO.C(Cl)Cl.O.[Ni](Cl)Cl>[CH3:3][C:4]1[N:9]=[C:8]([N:10]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([NH2:25])=[C:6]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:5]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 540930236-methyl-N4-(2-methylpropyl)-3-nitro-N2, N2-bis(phenylmethyl)pyridine-2,4-diamine

Product 1

HCID 538812726-Methyl-N4-(2-methylpropyl)-N2, N2-bis(phenylmethyl)pyridine-2,3,4-triamineYield 85.1%

Reagents, catalysts & solvents 3

HCID 16212333Nickel chloride hydrateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (585 mg, 16 mmole) was added to a solution of nickel (II) chloride hydrate (1.02 g, 4.3 mmole) in methanol (100 mL). The addition caused a black solid to form along with gas evolution. The resulting heterogeneous mixture was stirred at ambient temperature for 30 minutes. A solution containing 6-methyl-N4 -(2-methylpropyl)-3-nitro-N2, N2 -bis(phenylmethyl)pyridine-2,4-diamine (3.47 g, 8.6 mmole) in methylene chloride (20 mL) was added followed by the addition of sodium borohydride (1.37 g, 36 mmole). The reaction mixture was stirred at ambient temperature for about 30 minutes then eluted through a layer of silica gelwith a methanol/methylene chloride mixture. The filtrate was concentrated under vacuum. The resulting residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried with magnesium sulfate and concentrated under vacuum to provide 2.74 g of the desired product as a green foam.

Workup

  1. additionThe addition
  2. customto form along with gas evolution
  3. additionwas added
  4. stirringThe reaction mixture was stirred at ambient temperature for about 30 minutes
  5. washthen eluted through a layer of silica gelwith a methanol/methylene chloride mixture
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe resulting residue was partitioned between ethyl acetate and water
  8. customThe ethyl acetate layer was separated
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c3cd4a12cc5a41c396a2f0862c202ced
Source dataset
uspto-grants-1995_08
Patent number
US05446153

Reaction notes

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