Diethylamine → Allyl-[2-(2-diethylamino-ethoxy)-5-nitro-benzyl]-methyl-amine

HRID 2279212Notes

Reaction equation

HRID 2279212 reaction equation
[CH2:1]([N:4]([CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[O:16][CH2:17][CH2:18]Cl)[CH3:5])[CH:2]=[CH2:3].[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>CC(N(C)C)=O>[CH2:1]([N:4]([CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[O:16][CH2:17][CH2:18][N:22]([CH2:23][CH3:24])[CH2:20][CH3:21])[CH3:5])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 57341999HCID 57341999, compound

Product 1

HCID 57911959Allyl-[2-(2-diethylamino-ethoxy)-5-nitro-benzyl]-methyl-amineYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (xxiv) (1 g, 3.68 mmol) in DMA (10 mL) was added diethylamine (7.36 mmol) and the resulting mixture was stirred overnight at 60° C. The reaction mixture was quenched with water. The product was extracted with CH2Cl2 thrice and the combined organic extracts were washed with H2O followed by brine, dried over Na2SO4 and concentrated under reduced pressure to furnish without purification 750 mg of compound (xxv) in 70% yield. MS (m/z) 322 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionThe product was extracted with CH2Cl2 thrice
  3. washthe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55dba0935d844c9e8a1288500d1edb78
Source dataset
uspto-grants-2015_09
Patent number
US09133214B2

Reaction notes

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