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

HRID 1095830Notes

Reaction equation

HRID 1095830 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>>[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

3

Reactant 2

HCID 8082PiperidineHCID 158955201-(3-Chloropropoxy)-4-iodobenzene

Product 1

HCID 23047731-[3-(4-Iodophenoxy)propyl]piperidineYield 72.1%

Conditions

Temperature
85 °C

Procedure

1-[(3-chloropropyl)oxy]-4-iodobenzene (10 g, 33.7 mmol) and piperidine (2.87 g, 67.4 mmol) were mixed, and stirred at 85° C. for 4 hours. After cooled to room temperature, this was concentrated, and the residue was dissolved in ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline, and the organic layer was dried with sodium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=50/50 to chloroform/methanol=10/1) to obtain the entitled compound (8.39 g, 72%) as a brown solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthis was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated saline
  5. dry with materialthe organic layer was dried with sodium sulfate
  6. customThe solvent was evaporated off
  7. customthe residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=50/50 to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-caa1868cda204496aeafa1ddeaad0e28
Source dataset
uspto-grants-2012_03
Patent number
US08138206B2

Reaction notes

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