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

HRID 1820863Notes

Reaction equation

HRID 1820863 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

65.0 mL (65.0 mmol) of a 1M borane-THF solution is added dropwise at ambient temperature to a solution of 3.70 g (13.7 mmol) 2-(2-chloro-4-nitrophenyl)-N,N-diethylacetamide (VI.1.b) in 130 mL of THF and the mixture is 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, activity II-III) with petroleum ether/ethyl acetate (4:1) as eluant. Yield: 2.10 g (60% of theory); Rf value: 0.65 (Alox, petroleum ether/ethyl acetate=3:1); C12H17ClN2O2.

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-a3b9653ea0214fc1aa30bb953898ad9b
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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