Hydrochloric Acid → Hydrochloric Acid

HRID 2225303Notes

Reaction equation

HRID 2225303 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:11][C@H:10]1[CH2:20][CH:21]([OH:25])[CH:22]([CH3:24])[CH3:23])C1C=CC=CC=1.[ClH:33]>C(O)C.C(O)(=O)C.CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:11][C@H:10]1[CH2:20][CH:21]([OH:25])[CH:22]([CH3:24])[CH3:23].[ClH:33]

Participants

8

Reactant 2

HCID 313Hydrochloric AcidHCID 69286681HCID 69286681, compound

Product 2

HCID 313Hydrochloric AcidHCID 69285520HCID 69285520, compound

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Examples 11p and 11q, Step 9: To a solution of the isomeric mixture of 1-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-ol (166 mg, 0.38 mmoles) in 5 ml of ethanol and 1 ml of acetic acid was added about 150 mg of Pd(OH)2 on carbon (20%, wet, Aldrich), and the mixture was stirred under hydrogen (52 psi) for 24 hours. After removal of the catalyst by filtration. The solvents were evaporated off to give an oily residue. The residue was dissolved in methanol and 1 ml of 1N—HCl was added. It was evaporated and azeotroped with toluene twice to remove the excess acid and water, and dried under vacuum to give 1-((1S,2S,5R)-2-amino-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-ol as a bis-HCl salt.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customThe solvents were evaporated off
  4. customto give an oily residue
  5. customIt was evaporated
  6. customazeotroped with toluene twice
  7. customto remove the excess acid and water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-1e5bf165dcaa46069aadb45fa45912ac
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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