HCID 178418361, compound → HCID 178481017, compound

HRID 2364702Notes

Reaction equation

HRID 2364702 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:21][N:18]1[CH2:17][CH2:16][N:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10][CH2:11]2)[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178481019HCID 178481019, compound

Product 1

HCID 178481017HCID 178481017, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(trans)-N,N-dibenzyl-4-(4-methylpiperazin-1-yl)cyclohexanamine 17a (3.35 g, 8.90 mmol) was dissolved in 20 mL of methanol followed by the addition of palladium/carbon (335 mg, 10%), filled with hydrogen three times. The reaction solution was reacted at 3 atmosphere for 12 hours and filtered. The filtrate was concentrated under reduced pressure followed by the addition of 10 mL of 1 M hydrochloric acid and extracted with dichloromethane (30 mL×3). The aqueous phase was added dropwise with saturated aqueous sodium carbonate solution to adjust pH to 11, extracted with dichloromethane (50 mL×3). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and was concentrated under reduced pressure to obtain the crude title compound (trans)-4-(4-methylpiperazin-1-yl)cyclohexanamine 17b (0.82 g, yield: 46.7%) as a yellow oil liquid, which was used in the next step without further furification.

Workup

  1. customThe reaction solution was reacted at 3 atmosphere for 12 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionfollowed by the addition of 10 mL of 1 M hydrochloric acid
  5. extractionextracted with dichloromethane (30 mL×3)
  6. additionThe aqueous phase was added dropwise with saturated aqueous sodium carbonate solution
  7. extractionextracted with dichloromethane (50 mL×3)
  8. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1a602d802494fdb98b8a641bbda755e
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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