HCID 178459268, compound → HCID 178459266, compound

HRID 2356290Notes

Reaction equation

HRID 2356290 reaction equation
C([N:8]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([OH:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]1)CC1C=CC=CC=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].C(O)C>[NH2:8][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([OH:25])([CH3:23])[CH3:24])[CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 178459268HCID 178459268, compound

Product 1

HCID 178459266HCID 178459266, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

3.85 g of trans-2-{4-[N,N-dibenzylamino]cyclohexyl}propan-2-ol (11.40 mmol) was combined with 3.3 g of 20 wt % palladium hydroxide and dissolved with 100 mL of anhydrous ethyl alcohol. The mixture was flushed with H2 (4×) before a H2 balloon was inserted into the reaction and allowed to stir overnight. N2 was bubbled through for about 20 minutes and the catalyst was filtered off. The reaction was washed with methanol. The filtrate was concentrated in vacuo and redissolved in acetonitrile and sonicated which produced a white solid. The mixture was filtered and 0.67 g of white product was obtained (37% yield).

Workup

  1. customThe mixture was flushed with H2 (4×) before a H2 balloon
  2. customwas inserted into the reaction
  3. customN2 was bubbled through for about 20 minutes
  4. filtrationthe catalyst was filtered off
  5. washThe reaction was washed with methanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionredissolved in acetonitrile
  8. customsonicated which
  9. customproduced a white solid
  10. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-b2e988344e594d5cb713738af8d4bbb1
Source dataset
uspto-grants-2010_07
Patent number
US07759342B2

Reaction notes

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