Reaction #2186210

Reaction equation

3-Piperazin-1-yl-phenol

K2CO3

2-(3-bromo-propoxy)-tetrahydro-pyran

→

desired product

Yield 49.4%

3-{4-[3-(Tetrahydro-pyran-2-yloxy)-propyl]-piperazin-1 -yl}-phenol

Yield 49.4%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturecooled below 5° C
2. 2
   Extractionextracted with AcOEt after dilution with saline
3. 3
   DryingThe organic phase is dried over sodium sulfate
4. 4
   Otherevaporated
5. 5
   Otherthe residue column chromatographed (silica gel, AcOEt/EtOH 95:5)

Procedure

712 mg (4 mmol) 3-Piperazin-1-yl-phenol are dissolved in 30 mL DMF under argon and cooled below 5° C. After addition of 1.38 g (2.5 eq.) K2CO3, 166 mg (0.25 eq.) KI and 888 mg (1 eq.) 2-(3-bromo-propoxy)-tetrahydro-pyran, the suspension is stirred at room temperature for 20 hours, then extracted with AcOEt after dilution with saline. The organic phase is dried over sodium sulfate, evaporated and the residue column chromatographed (silica gel, AcOEt/EtOH 95:5) to yield 630 mg (48%) desired product as a light yellowish resin.

Source