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

HRID 322159Notes

Reaction equation

HRID 322159 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

4-Methyl-4-phenylpiperidine (1.00 g, 5.70 mmol, 1.00 equiv), 3-bromopropylamine hydrobromide (1.87 g, 8.55 mmol, 1.00 equiv) and potassium carbonate (1.97 g, 14.2 mmol, 2.5 equiv) were stirred in refluxing dioxane (20 mL) for 36 hours. After removal of the solvent, water (50 mL) was added and the pH was adjusted to 11-12 by addition of 1N aqueous NaOH. The mixture was extracted with CH2Cl2 (150 mL+3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, CHCl3-MeOH—NH3 (2M in MeOH) 100:20:10) to give 241 mg (18%) of colorless oil, which was characterized spectroscopically.

Workup

  1. customAfter removal of the solvent, water (50 mL)
  2. additionwas added
  3. additionthe pH was adjusted to 11-12 by addition of 1N aqueous NaOH
  4. extractionThe mixture was extracted with CH2Cl2 (150 mL+3×100 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, CHCl3-MeOH—NH3 (2M in MeOH) 100:20:10)

Sources & evidence

ORD record
ord-d28f445452514540aec911c29a96fbab
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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