Sodium Hydroxide → N-Methyl-3-(2-nitro-5-phenoxy-benzylamino)-N-phenyl-propionamide

HRID 390200Notes

Reaction equation

HRID 390200 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[NH2:19][CH2:20][CH2:21][C:22]([N:24]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH3:25])=[O:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH3:25][N:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:22](=[O:23])[CH2:21][CH2:20][NH:19][CH2:6][C:5]1[CH:8]=[C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride2×HCID 167934313-Amino-N-cyclohexyl-N-methyl-propionamideHCID 442030822-Nitro-5-phenoxybenzaldehyde

Product 1

HCID 58625076N-Methyl-3-(2-nitro-5-phenoxy-benzylamino)-N-phenyl-propionamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Nitro-5-phenoxy-benzaldehyde (2.14 g, 0.00882 mol) was added to a solution of 3-amino-N-cyclohexyl-N-methyl-propionamide (1.5 g, 0.00882 mol) in 100 mL of 1,2-dichloroethane, and the mixture was stirred at 80° C. for 1 hour. Sodium triacetoxyborohydride (2.87 g, 0.00882 mol) was added at room temperature, and the reaction mixture was stirred for 15 h. Additional sodium triacetoxyborohydride (1 g) was added, and the reaction mixture was stirred another 20 h at room temperature. To the reaction mixture was added 10% aqueous NaOH solution (50 mL), and the mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered, and concentrated to yield a residue which was purified by column chromatography over silica gel using 97:3 CH2Cl2:MeOH as the eluent. The product containing fractions were combined and evaporated to yield a side product (MW 638). The residue was further purified by column chromatography over silica gel using 97:3 CH2Cl2:MeOH. The product containing fractions were combined and evaporated to yield a residue. The fractions containing impure product were combined and evaporated to yield a second residue, which was purified by silica gel chromatography to yield additional desired product.

Workup

  1. stirringthe reaction mixture was stirred for 15 h
  2. stirringthe reaction mixture was stirred another 20 h at room temperature
  3. extractionthe mixture was extracted with CH2Cl2
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a residue which
  9. customwas purified by column chromatography over silica gel using 97:3 CH2Cl2
  10. additionThe product containing fractions
  11. customevaporated
  12. customto yield a side product (MW 638)
  13. customThe residue was further purified by column chromatography over silica gel using 97:3 CH2Cl2
  14. additionThe product containing fractions
  15. customevaporated
  16. customto yield a residue
  17. additionThe fractions containing impure product
  18. customevaporated
  19. customto yield a second residue, which
  20. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-0a8858f0ada843b8b51f9f6c6d0a59c1
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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