Iodoethane → HCID 69663289, compound

HRID 2212098Notes

Reaction equation

HRID 2212098 reaction equation
[C:1]1([S:7]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][OH:21])[CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24](I)[CH3:25]>>[C:1]1([S:7]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][O:21][CH2:24][CH3:25])[CH2:15]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 69662722HCID 69662722, compound

Product 1

HCID 69663289HCID 69663289, compound

Procedure

Sodium hydride (55 mg of 60% dispersion in oil) was washed with i-hexane and treated with tetrahydrofuran (3 ml). [1-(4-Benzenesulfonyl-4-methyl-pentyl)-piperidin-3-yl]-methanol (95 mg, 0.28 mmol) was added and the mixture was stirred at room temperature for 10 min. Ethyl iodide (0.5 ml) was added to the mixture that was stirred for 5 hours. The reaction mixture was quenched with 25% ammonia and extracted into dichloromethane. The combined organic extract were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol) to give to give the title compound.

Workup

  1. washSodium hydride (55 mg of 60% dispersion in oil) was washed with i-hexane
  2. additiontreated with tetrahydrofuran (3 ml)
  3. stirringwas stirred for 5 hours
  4. customThe reaction mixture was quenched with 25% ammonia
  5. extractionextracted into dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwere dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol)
  10. customto give

Sources & evidence

ORD record
ord-5edfe6d758464444b0827c68c524666c
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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