Reaction #433622

Reaction equation

ammonium chloride

Phosphorous oxycloride

N-methyl-N-(4-chlorobutyl)amine hydrochloride

triethyl amine

→

oil

Yield 85.0%

N-methyl-N-(4-chlorobutyl) phosphoramidic dichloride

Yield 85.0%

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   TemperatureWarmed
2. 2
   Otherreaction to 0° C.
3. 3
   Otherslowly to room temperature
4. 4
   OtherAllowed reaction
5. 5
   workup.ADDITIONThe reaction mixture was poured over ice
6. 6
   Otherseparated layers
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Concentrationconcentrated
9. 9
   OtherPurified by silica gel flash chromatography (3:1 Hex/EtOAc)

Procedure

N-methyl-N-(4-chlorobutyl)amine hydrochloride (2.0 g, 12.73 mmol) was dissolved in 20 mL of anhydrous CH2Cl2 and cooled to −40° C. Phosphorous oxycloride (1.2 mL, 12.73 mmol) was added neat followed by the drop wise addition of triethyl amine (3.6 mL, 25.46 mmol) in 5 mL of CH2Cl2. Warmed reaction to 0° C. and slowly to room temperature. Allowed reaction to stir at room temperature for 6 hours. The reaction mixture was poured over ice, added saturated ammonium chloride and separated layers. Extracted water layer 3× with CH2Cl2, combined organic layers, dried over anhydrous sodium sulfate and concentrated under reduce pressure. Purified by silica gel flash chromatography (3:1 Hex/EtOAc) to yield a clear oil (2.57 g, 85%).

Source