Hydrochloric Acid → (R)-1-(pyrrolidin-3-yl)piperidine

HRID 478933Notes

Reaction equation

HRID 478933 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9]1)C1C=CC=CC=1.[ClH:19]>CCO.[OH-].[OH-].[Pd+2]>[ClH:19].[NH:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:9]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 69830750(3R)-1-(1-benzyl-pyrrolidin-3-yl)-piperidine

Product 2

HCID 313Hydrochloric AcidHCID 7176312(R)-1-(pyrrolidin-3-yl)piperidineYield 151.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Compound 7 (1.4 g, 6.0 mmol) was added dropwise into a flask equipped with a H2 balloon and containing the mixture of Pd(OH)2 (400 mg, 20% on carbon) and HCl (1.15 mL, 35% in H2O, 19.5 mmol) in EtOH (50 mL). The mixture was stirred under H2 at 50° C. for 10 h. Solid was filtered out and washed with hot HOCH3 (2×10 mL). The combined liquid was evaporated to dryness to give HCl salt of (3R)-1-pyrrolidin-3-yl-piperidine 9 (1.4 g, 100%).

Workup

  1. customequipped with a H2 balloon
  2. additioncontaining
  3. filtrationSolid was filtered out
  4. washwashed with hot HOCH3 (2×10 mL)
  5. customThe combined liquid was evaporated to dryness

Sources & evidence

ORD record
ord-9f840aed95604e73a9ad5714cc0fda59
Source dataset
uspto-grants-2003_11
Patent number
US06642232B2

Reaction notes

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