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

HRID 2088840Notes

Reaction equation

HRID 2088840 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

The following reaction was completed under N2. A mixture of 3-(3-formyl-4-nitro-phenoxy)-benzonitrile (0.056 mol) and propylamine (0.059 mol) in DCE (450 ml) was stirred at room temperature, then NaBH(OAc)3 (0.063 mol) was added. 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: CH2Cl2/CH3OH 99/1). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

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

Sources & evidence

ORD record
ord-014c7dca07e144cd9c7715402b2c2187
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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