Hydrochloric Acid → HCID 23589106, compound

HRID 489894Notes

Reaction equation

HRID 489894 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[C:21]4[C:26]([CH:27]=[C:28]5[C:33]=3[CH:32]=[CH:31][CH:30]=[CH:29]5)=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:19])[CH2:14][CH2:13]2)[CH2:7]1)=[O:5])C.Cl>O1CCOCC1>[CH:32]1[C:33]2[C:28](=[CH:27][C:26]3[C:21]([C:20]=2[C:18]([N:15]2[CH2:14][CH2:13][CH:12]([N:8]4[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]4)[CH2:17][CH2:16]2)=[O:19])=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86589864HCID 86589864, compound

Product 1

HCID 23589106HCID 23589106, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

(3R)-1′-(Anthracene-9-carbonyl)-[1,4′]bipiperidinyl-3-carboxylic acid ethyl ester (containing a small amount of the corresponding isopropyl ester) (10 g, approx. 22 mmol) was dissolved with warming in dioxane (50 mL) and 2N hydrochloric acid (50 mL) was added. The clear yellow solution was heated at 110° C. (slight reflux) and a pinkish red color soon developed. After 165 min the solution was allowed to cool to ambient temperature. After standing overnight the dioxane was evaporated and an oily solid precipitated out. The mixture was washed with dichloromethane and the insoluble oil was separated from the aqueous layer, dissolved in a dioxane-water mixture (100 mL), xylene (100 mL) was added and the mixture was evaporated to dryness, finally under high vacuum, to give the title compound as a yellow foam which was used in the following procedure without further purification.

Workup

  1. dissolutionwas dissolved
  2. temperature(slight reflux)
  3. temperatureto cool to ambient temperature
  4. waitAfter standing overnight
  5. customthe dioxane was evaporated
  6. customan oily solid precipitated out
  7. washThe mixture was washed with dichloromethane
  8. customthe insoluble oil was separated from the aqueous layer
  9. dissolutiondissolved in a dioxane-water mixture (100 mL), xylene (100 mL)
  10. additionwas added
  11. customthe mixture was evaporated to dryness, finally under high vacuum

Sources & evidence

ORD record
ord-36862b7a42aa4c6888118a056af17414
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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