Potassium Carbonate → HCID 203693, compound

HRID 396614Notes

Reaction equation

HRID 396614 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O1CCOCC1.[I-].[K+]>[OH:17][CH2:16][CH2:15][CH2:14][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 698734-Phenylpiperidine

Product 1

HCID 203693HCID 203693, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4-phenylpiperidine (3.00 g, 18.6 mmol, 1.00 equiv), 3-bromopropan-1-ol (2.12 mL, 22.3 mmol, 1.20 equiv), potassium carbonate (12.8 g, 93.0 mmol, 5.00 equiv), and potassium iodide (124 mg, 0.74 mmol, 0.04 equiv) in n-butanol (50 mL) and 1,4-dioxane (50 mL) was stirred at reflux under argon for 48 hours. The mixture was cooled to room temperature and concentrated. Water (50 mL) was added and the mixture was extracted with CH2Cl2 (4×100 mL). The combined organic solutions were dried over MgSo4 and concentrated. The residue was crystallized from ethyl acetate to give 3.36 g (82%) of tan solid, which was characterized spectroscopically.

Workup

  1. temperatureat reflux under argon for 48 hours
  2. concentrationconcentrated
  3. additionWater (50 mL) was added
  4. extractionthe mixture was extracted with CH2Cl2 (4×100 mL)
  5. customThe combined organic solutions were dried over MgSo4
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-7a39f3a5a176470fbb395e559c61eba9
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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