Thionyl Chloride → HCID 54362683, compound

HRID 266042Notes

Reaction equation

HRID 266042 reaction equation
S(Cl)([Cl:3])=O.O[C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH:9]3[CH2:16][CH2:17][N:18]3[CH2:26][CH:25]4[CH2:27][CH:21]5[CH2:22][CH:23]([CH2:28][CH:19]3[CH2:20]5)[CH2:24]4)[CH2:7]1)[CH2:13]2>>[Cl:3][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH:9]3[CH2:16][CH2:17][N:18]3[CH2:26][CH:25]4[CH2:27][CH:21]5[CH2:22][CH:23]([CH2:28][CH:19]3[CH2:20]5)[CH2:24]4)[CH2:7]1)[CH2:13]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 9862309HCID 9862309, compound

Product 1

HCID 54362683HCID 54362683, compound

Procedure

Thionyl chloride 5 ml was added to 4-[2-(5-hydroxy-2-adamantyl)-ethyl]-4-azatricyclo[4.3.1.1 3.8 ] undecane 105 mg obtained in example 8 and refluxed for 4 hours. Reaction mixture was concentrated in vacuo and saturated sodium bicarbonate was added to the residue to set to alkaline pH, then extracted with chloroform. The extract was dried by adding ahnydrous sodium sulfate. After removal of drying agent, the filtrate was concentrated in vacuo, and the residue was purified by means of silica gel column chromatography (Wako gel, C200, chloroform: methanol=50:1-20:1) to obtain the product as a mixture of stereoisomer. (a mixture of stereoisomer 1:1 measured by gas chromatography)

Workup

  1. temperaturerefluxed for 4 hours
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo and saturated sodium bicarbonate
  4. additionwas added to the residue
  5. extractionextracted with chloroform
  6. customThe extract was dried
  7. additionby adding ahnydrous sodium sulfate
  8. customAfter removal
  9. customof drying agent
  10. concentrationthe filtrate was concentrated in vacuo
  11. customthe residue was purified by means of silica gel column chromatography (Wako gel, C200, chloroform: methanol=50:1-20:1)
  12. customto obtain the product
  13. additionas a mixture of stereoisomer
  14. addition(a mixture of stereoisomer 1:1

Sources & evidence

ORD record
ord-3958fe963d4d447ca2d48c2bdd299bdc
Source dataset
uspto-grants-1997_07
Patent number
US05650406

Reaction notes

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