Potassium Carbonate → 4,4-bis(4-methoxyphenyl)piperidine

HRID 396658Notes

Reaction equation

HRID 396658 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br.Br[CH2:25][CH2:26][CH2:27][NH2:28].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1.[NH2:28][CH2:27][CH2:26][CH2:25][N:12]1[CH2:13][CH2:14][C:9]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromideHCID 113009584,4-bis(4-methoxyphenyl)piperidine

Product 2

HCID 113009584,4-bis(4-methoxyphenyl)piperidineHCID 23004163HCID 23004163, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4,4-bis-(4-Methoxyphenyl)piperidine (9.01 g, 30.3 mmol, 1.00 equiv), 3-bromopropylamine hydrobromide (6.66 g, 30.3 mmol, 1.00 equiv) and potassium carbonate (5.02 g, 36.3 mmol, 1.20 equiv) were stirred in refluxing anhydrous 1,4-dioxane (200 mL) for 12 hours. After removal of dioxane, water (200 mL) was added and the pH was adjusted to 11-12 by addition of 1 N aqueous NaOH. The mixture was extracted with CH2Cl2 (4×200 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 6.50 g of 4,4-bis-(4-methoxyphenyl)piperidine and 2.70 g (25%, 90% after correction for recovered starting material) of 1-(3-aminopropyl)-4,4-bis-(4-methoxyphenyl)piperidine (colorless oil), which was characterized spectroscopically.

Workup

  1. customAfter removal of dioxane, water (200 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 (4×200 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-cee518122ff54051b67ca3d2de45e62e
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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