Borane;tetrahydrofuran → [2-(2-Chloro-4-nitrophenyl)ethyl]diethylamine

HRID 735122Notes

Reaction equation

HRID 735122 reaction equation
B.C1COCC1.[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH2:17][C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=O>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH2:17][CH2:18][N:20]([CH2:21][CH3:22])[CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 688195332-Chloro-N,N-diethyl-4-nitrobenzeneacetamide

Product 1

HCID 68816908[2-(2-Chloro-4-nitrophenyl)ethyl]diethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

65 mL (65 mmol) of a 1M borane-THF solution is added dropwise to a solution of 3.7 g (13.67 mmol) of 2-(2-chloro-4-nitrophenyl)-N,N-diethylacetamide in 130 mL of THF at ambient temperature and stirred for 4 hours. Then the reaction mixture is evaporated down and the residue is combined with 15 mL of methanol and 15 mL of dilute hydrochloric acid. The mixture is then stirred for 15 minutes at 100° C., cooled, and diluted with water. Then the mixture is made alkaline with sodium carbonate solution and extracted twice with ethyl acetate. The combined organic phases are extracted twice with water and once with saturated saline solution and dried over sodium sulfate. The purification is carried out by column chromatography on Alox, neutral, act. II-III (eluant: petroleum ether/ethyl acetate (4:1)). Yield: 2.1 g (59.8% of theory); C12H17ClN2O2 (M=256.73); Rf value: 0.63 (Alox, petroleum ether/ethyl acetate (3:1)).

Workup

  1. customThen the reaction mixture is evaporated down
  2. stirringThe mixture is then stirred for 15 minutes at 100° C.
  3. temperaturecooled
  4. additiondiluted with water
  5. extractionextracted twice with ethyl acetate
  6. extractionThe combined organic phases are extracted twice with water and once with saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. customThe purification

Sources & evidence

ORD record
ord-f5d705e770c843f597c2aa4c71c8e792
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…