Hydrochloric Acid → HCID 23589145, compound

HRID 489906Notes

Reaction equation

HRID 489906 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([C:30]4[CH:35]=[C:34]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[N:33]=[C:32]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[CH:31]=4)=[O:29])[CH2:24][CH2:23]3)[CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[C:42]1([C:32]2[CH:31]=[C:30]([C:28]([N:25]3[CH2:24][CH2:23][CH:22]([N:18]4[CH2:19][CH2:20][CH2:21][C@@H:16]([C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[O:15])[CH2:17]4)[CH2:27][CH2:26]3)=[O:29])[CH:35]=[C:34]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:33]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 69694770HCID 69694770, compound

Product 1

HCID 23589145HCID 23589145, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

(3R)-4-[1′-(2,6-Diphenyl-pyridine-4-carbonyl)-[1,4′]bipiperidinyl-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (1.78 g, 2.79 mmol) was dissolved in ethyl acetate (25 mL) and cooled to −78° C. under nitrogen. Hydrogen chloride was passed in for several minutes and formation of a white precipitate was observed which redissolved almost immediately. When the solution was saturated with hydrogen chloride it was allowed to warmed to ambient temperature and after 1 h the solvent was evaporated in a stream of dry nitrogen, passing the evolved gasses to a water scrubber. A loose yellowish powder remained (2.02 g, >100% calculated as trishydrochloride). This was dissolved in water, basified by the addition of 2M sodium hydroxide (to pH 13.5) and extracted with dichloromethane (×3). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give the title compound as a powdery foam (1.37 g, 91%).

Workup

  1. customwas passed in for several minutes and formation of a white precipitate
  2. dissolutionredissolved almost immediately
  3. temperatureto warmed to ambient temperature and after 1 h the solvent
  4. customwas evaporated in a stream of dry nitrogen
  5. dissolutionThis was dissolved in water
  6. additionbasified by the addition of 2M sodium hydroxide (to pH 13.5)
  7. extractionextracted with dichloromethane (×3)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-a59e85c962ed4379a1c5d6bae3104b0e
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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