Potassium Carbonate → HCID 69072933, compound

HRID 2099028Notes

Reaction equation

HRID 2099028 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1>CN(C=O)C>[O:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH:25]1[O:24][CH2:23][CH2:22][CH2:21][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27365971-(3-Hydroxyphenyl)piperazineHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Product 1

HCID 69072933HCID 69072933, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. temperaturecooled below 5° C
  2. extractionextracted with AcOEt after dilution with saline
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customthe residue column chromatographed (silica gel, AcOEt/EtOH 95:5)

Sources & evidence

ORD record
ord-1c25976a6a2647f7af53a1dd9b8001a2
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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