Dimethylamine → n,n-Dimethyl-2-(4-nitrophenyl)ethanamine

HRID 1804710

Reaction equation

HRID 1804710 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH2:13]([N:15](CC)[CH2:16]C)C.CNC.O1CCCC1>C(#N)C>[CH3:13][N:15]([CH3:16])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 792664-Nitrophenethyl bromide

Product 1

HCID 220557n,n-Dimethyl-2-(4-nitrophenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A pressure tube was charged with 1-(2-bromoethyl)-4-nitrobenzene (1 g, 4.35 mmol) in acetonitrile (5 mL). Triethylamine (2.4 mL) and dimethylamine, 2M in tetrahydrofuran (0.784 g, 17.39 mmol) were added, and the sealed tube was stirred at ambient temperature for 2 days. The reaction mixture was partitioned between dilute NaHCO3 solution and ethyl acetate, then extracted another two times with ethyl acetate. The product was then extracted into 2N HCl (2×25 mL). Following neutralization with 2N NaOH, the aqueous mixture was extracted with ethyl acetate (3×). The extracts were dried (Na2SO4), filtered and concentrated to give the title compound. MS (ESI(+)) m/e 194.9 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between dilute NaHCO3 solution and ethyl acetate
  2. extractionextracted another two times with ethyl acetate
  3. extractionThe product was then extracted into 2N HCl (2×25 mL)
  4. extractionthe aqueous mixture was extracted with ethyl acetate (3×)
  5. dry with materialThe extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cd3e9be9e3054569bbbfb06b5a17910c
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Linked notes

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