4-Nitrobenzaldehyde → N-ethyl-N-[(4-nitrophenyl)methyl]ethanamine

HRID 2352989Notes

Reaction equation

HRID 2352989 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH2:12]([N:14]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:15][CH3:16])[CH3:13]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 8021DiethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 412435N-ethyl-N-[(4-nitrophenyl)methyl]ethanamineYield 137.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2.11 g (14 mmol) of 4-nitrobenzaldehyde in 50 mL dichloroethane was added diethylamine (1.13 g, 15.4 mmol) followed by sodium triacetoxyborohydride (4.45 g, 21 mmol). The mixture was stirred at room temperature overnight. A solution of saturated aqueous sodium bicarbonate (25 mL) was added to the reaction mixture and the resulting solution was extracted with ethyl acetate (1×150 mL, 2×50 mL). The combined organic extract was dried (sodium sulfate), filtered, and solvent removed under reduced pressure to provide crude N-ethyl-N-(4-nitrobenzyl)ethanamine as an oil (4.0 g). The material was used in the next step without further purification.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate (1×150 mL, 2×50 mL)
  2. extractionThe combined organic extract
  3. dry with materialwas dried (sodium sulfate)
  4. filtrationfiltered
  5. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-1ce3b694acaa4426a245602465655160
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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