1-Butanol → HCID 59837375, compound

HRID 272921Notes

Reaction equation

HRID 272921 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CCC>[I-].[K+].O>[N:20]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 8082PiperidineHCID 10340Sodium CarbonateHCID 598375041-[4-(3-Bromo-propoxy)-phenyl]-cyclohexanecarbonitrile

Product 1

HCID 59837375HCID 59837375, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[4-(3-bromo-propoxy)-phenyl]-cyclohexanecarbonitrile (0.660 g, 2.0 mmol), piperidine (0.260 g, 3.0 mmol), sodium carbonate (0.320 g, 3 mmol), potassium iodide (20 mg) and 20 mL of butanol was heated for 4 h at 100° C. according to general procedure G. After cooling, water was added to quench the reaction and the mixture was extracted with DCM. The organics extracts were washed with a saturated aqueous solution of NaHCO3, water and dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (DCM and DCM/MeOH (10% NH3) to provide the title compound (0.440 g, 67%). 1H NMR (400 MHz, CDCl3) δ7.37 (d, 2H), 6.90 (d, 2H), 4.00 (t, 2H), 2.49-2.36 (m, 6H), 2.17-2.09 (m, 2H), 1.97 (qt, 2H), 1.88-1.67 (m, 7H), 1.62-1.55 (m, 4H), 1.47-1.40 (m, 2H), 1.32-1.20 (m, 1H).

Workup

  1. temperatureAfter cooling
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with DCM
  5. washThe organics extracts were washed with a saturated aqueous solution of NaHCO3, water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (DCM and DCM/MeOH (10% NH3)

Sources & evidence

ORD record
ord-8ab30aaaed0149749f8cce365fd74035
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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