Sodium Iodide → HCID 23091620, compound

HRID 272861Notes

Reaction equation

HRID 272861 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>CCOCC.CC(C)=O>[N:20]1([CH2:19][CH2:18][CH2:17][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:6][CH:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 198585061-(4-Hydroxyphenyl)cyclohexane-1-carbonitrile

Product 1

HCID 23091620HCID 23091620, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

1-(4-Hydroxyphenyl)cyclohexanecarbonitrile (1.70 g, 8.45 mmol), 1-(3-chloro-propyl)-pyrrolidine (1.87 g, 12.67 mmol), acetone (50 mL), sodium iodide (0.444 g, 2.96 mmol) and K2CO3 (5.45 g, 39.44 mmol) were heated to 50° C. overnight. The solvent was evaporated and the crude product was taken into DCM, washed with 0.5N NaOH, extracted with 0.5N HCl solution and washed with DCM. The aqueous layer was basified with 0.5N NaOH and extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered, washed with DCM and concentrated in vacuo to give a yellowish solid. The solid was slurried in ether, filtered, washed with ether to give the title compound as a white solid (1.34 g, 51%). 1H NMR (400 MHz, CDCl3) δ7.30 (d, 2H), 6.83 (d, 2H), 3.95 (t, 2H), 2.54 (t, 2H), 2.44 (m, 4H), 2.06 (m, 2H), 1.92 (m, 2H), 1.84-1.58 (m, 12H).

Workup

  1. customThe solvent was evaporated
  2. washwashed with 0.5N NaOH
  3. extractionextracted with 0.5N HCl solution
  4. washwashed with DCM
  5. extractionextracted with DCM
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. washwashed with DCM
  9. concentrationconcentrated in vacuo
  10. customto give a yellowish solid
  11. filtrationfiltered
  12. washwashed with ether

Sources & evidence

ORD record
ord-7455271772d146e9897db7d0f18329ba
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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