Potassium Carbonate → 4-Acetyl-1-(3-aminopropyl)-4-phenylpiperidine

HRID 322151

Reaction equation

HRID 322151 reaction equation
[C:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br.Br[CH2:18][CH2:19][CH2:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][N:7]([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 1015214-Acetyl-4-phenylpiperidine

Product 1

HCID 105874474-Acetyl-1-(3-aminopropyl)-4-phenylpiperidineYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Acetyl-4-phenylpiperidine (1.53 g, 7.50 mmol, 1.00 equiv, Aldrich), 3-bromopropylamine hydrobromide (1.64 g, 7.50 mmol, 1.00 equiv) and potassium carbonate (1.24 g, 9.00 mmol, 1.20 equiv) were stirred in refluxing 1,4-dioxane (50 mL) for 12 hours. After removal of dioxane, 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 (100 mL+3×50 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (EtOAc-MeOH—Et3N 100:40:20) to give 780 mg (40%) of colorless oil, which was characterized spectroscopically.

Workup

  1. customAfter removal of dioxane, 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 (100 mL+3×50 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (EtOAc-MeOH—Et3N 100:40:20)

Sources & evidence

ORD record
ord-6d7c7d93fb5f4da19e75f1fd2b63b7a6
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Linked notes

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