Piperidine → 1-[3-(4-Iodophenoxy)propyl]piperidine

HRID 33693Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC.O.[I-].[K+]>[I:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A suspension of 4-(3-chloro-1-propoxy)iodobenzene (5 g), piperidine (2.2 mL), sodium carbonate (2.7 g), and potassium iodide (140 mg) in n-butanol (30 mL) was heated in a 105° C. bath for 18 h. The resulting mixture was allowed to cool to room temperature, diluted with water (50 mL), and extracted with methylene chloride (2×20 mL). The combined organic phases were dried (magnesium sulfate), and evaporated in vacuo. Kugelrohr distillation of the residue (5 mm Hg, 260° C.) gave the title compound as a white crystalline solid (4.8 g).

Workup

temperatureto cool to room temperature
extractionextracted with methylene chloride (2×20 mL)
dry with materialThe combined organic phases were dried (magnesium sulfate)
customevaporated in vacuo
distillationKugelrohr distillation of the residue (5 mm Hg, 260° C.)

Sources & evidence

ORD record: ord-954f43423d5043489dc3b51ea2e8b455
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429586B2

Reaction notes

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