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

HRID 502745Notes

Reaction equation

HRID 502745 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.Cl.[CH3:25][NH:26][CH3:27]>ClCCl.O>[CH3:25][N:26]([CH3:27])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1

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 1-(3-chloropropoxy)-4-nitrobenzene (2 g, 9.27 mmol), potassium carbonate (7.69 g, 46.4 mmol) and acetonitrile (15 ml) was prepared and stirred in a tube. To the stirring solution dimethylamine hydrochloride (3.78 g, 46.4 mmol) was added quickly. The tube was sealed and the mixture was stirred while heating 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.

Workup

  1. customwas prepared
  2. customThe tube was sealed
  3. stirringthe mixture was stirred
  4. temperatureThe mixture was cooled well
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. customThe combined organics were dried
  7. customevaporated

Sources & evidence

ORD record
ord-a2f62a46f18f442c86c3a70fdf95179f
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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