Potassium Carbonate → 3-[4-(2-Fluoroethyl)piperazin-1-YL]propan-1-OL

HRID 1785127Notes

Reaction equation

HRID 1785127 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].C(=O)([O-])[O-].[K+].[K+].OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[F:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(#N)C>[F:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][OH:5])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 87238377HCID 87238377, compound

Product 1

HCID 451157673-[4-(2-Fluoroethyl)piperazin-1-YL]propan-1-OLYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

3-Bromopropan-1-ol (581 mg, 4.18 mmol) and potassium carbonate (2.88 g, 20.9 mmol) were added to a solution of 1-(2-fluoroethyl)-piperazine diTFA salt (1.5 g, 4.18 mmol) in acetonitrile (11 ml). The reaction mixture was stirred at 85° C. for 4 hours and then loaded directly onto a column and eluted with a mixture of methanol in methylene chloride (7/93) to give 3-[4-(2-fluoroethyl)piperazin-1-yl]propan-1-ol (721 mg, 91%). NMR Spectrum: (CDCl3) 1.72 (m, 2H); 2.58(m, 8H) 2.62 (m, 2H); 2.73 (t, 2H); 3.79 (t, 2H); 4.55 (dt, 2H). MS-EI: 191 [MH]+

Workup

  1. washeluted with a mixture of methanol in methylene chloride (7/93)

Sources & evidence

ORD record
ord-dadf50e5032348668ad75358a0b5fbde
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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