Thionyl Chloride → HCID 19032321, compound

HRID 266039Notes

Reaction equation

HRID 266039 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[CH2:24][CH:23]4[CH2:25][CH2:26][CH:20]([CH2:21][CH2:22]4)[CH2:19]3)[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[CH2:24][CH:23]4[CH2:25][CH2:26][CH:20]([CH2:21][CH2:22]4)[CH2:19]3)[CH2:7]1)[CH2:13]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19032326HCID 19032326, compound

Product 1

HCID 19032321HCID 19032321, compound

Procedure

Thionyl chloride 5 ml was added to 3-[2-(5-hydroxy-2-adamantyl) ethyl]-3-azabicyclo[3.2.2] nonane 59.5 mg obtained in example 2 and refluxed for 16 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: acetone=15:1) to obtain the product as a mixture of stereoisomer. (a mixture of stereoisomer 1:1 measured by gas chromatography)

Workup

  1. temperaturerefluxed for 16 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: acetone=15:1)
  12. customto obtain the product
  13. additionas a mixture of stereoisomer
  14. addition(a mixture of stereoisomer 1:1

Sources & evidence

ORD record
ord-2d5ad4e52e614195b2f76582c2a073c6
Source dataset
uspto-grants-1997_07
Patent number
US05650406

Reaction notes

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