Potassium Carbonate → 3-Aminopropyl-4-methyl-4-phenylpiperidine

HRID 2085399Notes

Reaction equation

HRID 2085399 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br.Br[CH2:16][CH2:17][CH2:18][NH2:19].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:19][CH2:18][CH2:17][CH2:16][N:5]1[CH2:4][CH2:3][C:2]([CH3:1])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 30195114-Methyl-4-phenylpiperidine

Product 1

HCID 107996093-Aminopropyl-4-methyl-4-phenylpiperidineYield 18.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-methyl-4-phenylpiperidine (1.00 g, 5.70 mmol), 3-bromopropylamine hydrobromide (1.87 g, 8.55 mmol) and potassium carbonate (1.97 g, 14.2 mmol) in refluxing dioxane (20 mL) was stirred for 36 hours. After removal of the solvent, water (50 mL) was added and the pH adjusted to 11-12 by the addition of 1 N aqueous NaOH. The mixture was extracted with CH2Cl2 (150 mL+3×100 mL) The combined organic solutions were dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (CHCl3/MeOH/2 N NH3 in MeOH 100/20/10), giving the desired product as a colorless oil (241 mg, 18%): 1H NMR δ 1.18 (s, 3 H), 1.61 (p, J=7 Hz, 2 H), 1.75 (m, 2 H), 2.10 (m, 2 H), 2.33 (t, J=7 Hz, 2 H), 2.40 (m, 2 H), 2.45 (m, 2 H), 2.72 (t, J=6 Hz, 2 H), 3.02 (br s, 2 H), 7.14 (m, 1 H), 7.30 (m, 4 H); 13C NMR δ 30.28, 36.78, 37.64, 41.51, 50.96, 57.51, 126.16, 126.40, 128.91, 149.20.

Workup

  1. customAfter removal of the solvent, water (50 mL)
  2. additionwas added
  3. additionthe pH adjusted to 11-12 by the addition of 1 N aqueous NaOH
  4. extractionThe mixture was extracted with CH2Cl2 (150 mL+3×100 mL) The combined organic solutions
  5. dry with materialwere dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (CHCl3/MeOH/2 N NH3 in MeOH 100/20/10)

Sources & evidence

ORD record
ord-be23ceb8080e4696826add304e712a4a
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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