Bromobenzene → 1-Phenylpiperidine

HRID 511888Notes

Reaction equation

HRID 511888 reaction equation
CC(C)([O-])C.[K+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>>[C:8]1([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7961Bromobenzene2×HCID 8082PiperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 200381-Phenylpiperidine

Conditions

Temperature
110 °C

Procedure

224 mg (2 mmoles) of potassium tert.-butoxide, 70 mg (2.5 mole % calculated for the bromobenzene substrate) of the catalyst of formula (I), 105 μl (1 mmole) of bromobenzene, 198 μl (2 mmoles) of piperidine and 5 ml of solvent were charged into an oven-dried Schlenk tube. The reaction mixture was heated on an oil bath at 110° C. for 24 hours, allowed then to cool to room temperature, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluant: hexane/ethyl acetate) to give the desired product; 1H NMR (300 MHz, CDCl3) δ 7.31-7.26 (m, 2H), 7.00-6.97 (m, 2H), 6.89-6.84 (m, 1H), 3.19 (t, J=5.6 Hz, 4H), 1.79-1.72 (m, 4H), 1.64-1.59 (m, 2H).

Workup

  1. additionwere charged into an oven-dried Schlenk tube
  2. temperatureto cool to room temperature
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluant: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4c6e1d83a7644f7694d6b675edb66098
Source dataset
uspto-grants-2015_08
Patent number
US09101920B2

Reaction notes

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