Propylamine → 3-(4-Nitro-3-propylaminomethyl-phenoxy)-benzonitrile

HRID 390218Notes

Reaction equation

HRID 390218 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])=O.[CH2:21]([NH2:24])[CH2:22][CH3:23].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[N+:18]([C:17]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])=[CH:4][C:3]=1[CH2:1][NH:24][CH2:21][CH2:22][CH3:23])([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 586250423-(3-Formyl-4-nitrophenoxy)-benzonitrile

Product 1

HCID 586250603-(4-Nitro-3-propylaminomethyl-phenoxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under N2, a mixture of 3-(3-formyl-4-nitrophenoxy)-benzonitrile (0.056 mol) and propylamine (0.059 mol) in DCE (450 mL) was stirred at room temperature, and then NaBH(OAc)3 (0.063 mol) was added, and the reaction mixture was stirred overnight at room temperature. A saturated NaHCO3 solution was added, and the layers were separated. The organic layer was dried, filtered off and the solvent was evaporated. The residue was purified over silica gel filter (eluent: 99:1 CH2Cl2:CH3OH). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customthe solvent was evaporated
  6. customThe residue was purified over silica gel
  7. filtrationfilter (eluent: 99:1 CH2Cl2:CH3OH)
  8. customThe purest product fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-413b8e15347a463facec50cac2ac503f
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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