Potassium Iodide → HCID 11741533, compound

HRID 2218235Notes

Reaction equation

HRID 2218235 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[C:16]1[C:17]([CH2:27]CCC2C=CC=CC=2)=C(C)[CH:19]=[CH:20][C:21]=1S([O-])(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH:37]12[CH2:42][CH:41]1[CH2:40][NH:39][CH2:38]2.[C:43](=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:51](#N)[CH3:52]>CN(C)C=O.O>[CH:37]12[CH2:42][CH:41]1[CH2:40][N:39]([CH2:27][CH2:17][CH:16]([C:10]1[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:21]1[CH:20]=[CH:19][CH:52]=[CH:51][CH:43]=1)[CH2:38]2

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 223352893-Azabicyclo[3.1.0]hexane hydrochlorideHCID 86606011HCID 86606011, compound

Product 1

HCID 11741533HCID 11741533, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropyl-p-toluene sulphonate (Prepared by following the process as described in EP 0 325 571, 0.486 gm, 1 mmol), 3-azabicyclo[3.1.0]hexane hydrochloride (Prepared by following the process as described in U.S. Pat. No. 4,183,857, 0.12 gm, 1 mmol), potassium carbonate (0.275 gm, 2 mmol), potassium iodide (0.17 gm, 1 mmol) in acetonitrile (10 ml) and dimethylformamide (10 ml) were refluxed for 15 hours at about 100° C. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated in vacuo to afford an oily residue, which was purified by column chromatography (silica gel 100-200 mesh), eluting the compound with 50-50 ethylacetate-hexane mixture.

Workup

  1. customPrepared
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customto afford an oily residue, which
  7. customwas purified by column chromatography (silica gel 100-200 mesh)
  8. washeluting the compound with 50-50 ethylacetate-hexane mixture

Sources & evidence

ORD record
ord-23ea20fcb6b746af88da24efbc34ccac
Source dataset
uspto-grants-2008_08
Patent number
US07410993B2

Reaction notes

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