Potassium Carbonate → HCID 203693, compound

HRID 382670Notes

Reaction equation

HRID 382670 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. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-749c9c9b63d144ae9901bbd7514e98b2
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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