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

HRID 382712Notes

Reaction equation

HRID 382712 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) wore 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 1 N 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 (2 M 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 1 N 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 (2 M in MeOH) 100:20:10)

Sources & evidence

ORD record
ord-5c504781adb74df09233c6b8ad93ec80
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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