Hydrochloric Acid → HCID 21241598, compound

HRID 579799Notes

Reaction equation

HRID 579799 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2([CH3:23])OCC[O:19]2)[CH2:14][CH2:13]1.Cl.[OH-].[Na+]>>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([C:18](=[O:19])[CH3:23])[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21241621HCID 21241621, compound

Product 1

HCID 21241598HCID 21241598, compoundYield 55.8%

Procedure

A mixture of 20.6 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-(2-methyl-1,3-dioxolan-2-yl)piperidine and 200 parts of a hydrochloric acid solution 2N was stirred and refluxed for 15 hours. After cooling, crushed ice was added. The whole was treated with a sodium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 10 parts (55.8%) of 1-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]ethanone as an oily residue (intermediate 87).

Workup

  1. temperaturerefluxed for 15 hours
  2. temperatureAfter cooling
  3. customcrushed ice
  4. additionwas added
  5. extractionThe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-6288f8c9f36145d7b04feb077cbbdd3d
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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