1,4-Cyclohexadiene → HCID 55287554, compound

HRID 2217890Notes

Reaction equation

HRID 2217890 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:9]2)C=CC=CC=1.C1CC=CCC=1>[OH-].[OH-].[Pd+2].C(O)C>[NH:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:9]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 28830263HCID 28830263, compound

Product 1

HCID 55287554HCID 55287554, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

3-[[(3S)-1-(Phenylmethyl)-3-pyrrolidinyl]amino]-propanenitrile (as described in WO2000075137) (0.6 g), 20% palladium hydroxide on carbon (0.15 g), 1,4 cyclohexadiene (3 mL) and ethanol (2 mL) were loaded into a 10 mL microwave vial, capped and heated at 100° C. for 90 minutes within a single mode microwave. The reaction mixture was filtered and the volatiles removed under vacuum to afford the sub-title compound (0.304 g).

Workup

  1. customcapped
  2. filtrationThe reaction mixture was filtered
  3. customthe volatiles removed under vacuum

Sources & evidence

ORD record
ord-cb7cfd7461a2447cbb1b5f87796adadf
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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