Acetonitrile → N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

HRID 2117619Notes

Reaction equation

HRID 2117619 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][CH2:11]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].C(#N)C.Cl.[CH3:25][NH:26][CH3:27]>ClCCl.O>[CH3:25][N:26]([CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:27]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Product 1

HCID 10353575N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-nitrophenoxy)propyl chloride (2 g, 9.27 mmol), potassium carbonate (7.69 g, 46.4 mmol) and acetonitrile (15 mL) were stirred in a sealed tube and dimethylamine hydrochloride (3.78 g, 46.4 mmol) added quickly. The mixture was stirred and heated overnight at 80° C. The mixture was cooled well before opening the pressure tube, then water and dichloromethane were added and the aqueous layer was extracted with dichloromethane. The combined organics were dried and evaporated giving the title product. 1H NMR (400 MHz, CDCl3): 1.95 (2H, t, J 7 Hz); 2.2 (6H, s); 2.35-2.45 (2H, m); 4.05 (2H, t, J 7 Hz); 6.9 (2H, d, J 8 Hz); 8.1 (2H, d, J 8 Hz).

Workup

  1. stirringThe mixture was stirred
  2. temperatureThe mixture was cooled well
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. customThe combined organics were dried
  5. customevaporated

Sources & evidence

ORD record
ord-85c41081802d4468b51ff3c612241fa3
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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