Water → 2-(3-chloropropyl)amino-N,N-dimethylbenzamide

HRID 2294147Notes

Reaction equation

HRID 2294147 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23].O>CN(C=O)C>[Cl:23][CH2:22][CH2:21][CH2:20][NH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 47781752-Amino-N,N-dimethylbenzamide

Product 1

HCID 214734352-(3-chloropropyl)amino-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-N,N-dimethylbenzamide (1.15 g, 6,97 mmol), prepared as in Example 22, potassium carbonate (1.44 g, 10.46 mmol) and 1-bromo-3-chloro-propane (0.7 mL, 7 mmol) in 10 mL of DMF was stirred at room temperature for 16 hours and then at 70° C. for an additional 4 hours. The mixture was poured into water and extracted with ethyl acetate (3×20 mL). The combined extract was washed with brine, dried (MgSO4) and concentrated to give 2-(3-chloropropyl)amino-N,N-dimethylbenzamide as a crude mixture.

Workup

  1. waitat 70° C. for an additional 4 hours
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed155e87aacb413ca9d91b34f14819fc
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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