Ethylene Glycol → 1-[1-(4-Bromo-phenyl)-pyrrolidin-3-yl]-piperidin

HRID 1916640Notes

Reaction equation

HRID 1916640 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C(O)CO.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH:21]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22]1>C(O)(C)C.CCOC(C)=O.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:21]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:22]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 230096171-(Pyrrolidin-3-yl)piperidine

Product 1

HCID 673648881-[1-(4-Bromo-phenyl)-pyrrolidin-3-yl]-piperidin

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

283 mg (1.00 mmol) 4-bromo-iodobenzene, 10 mg (0.05 mmol) CuI, 124 mg (2.00 mmol) ethyleneglycol and 424 mg (2.00 mmol) potassium phosphate are added to a reaction vessel, which is evacuated and rinsed with argon several times. Then 154 mg (1.00 mmol) 1-pyrrolidin-3-yl-piperidine in 1 mL isopropanol are added and the reaction is shaken for 15 h at 80° C. The reaction solution is diluted with EtOAc and extracted twice with 5% ammonia solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

Workup

  1. customwhich is evacuated
  2. washrinsed with argon several times
  3. extractionextracted twice with 5% ammonia solution
  4. dry with materialThe organic phase is dried over MgSO4

Sources & evidence

ORD record
ord-539a00bb81aa46a890b77bf29e4f2100
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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