Acetic Acid → HCID 69307251, compound

HRID 1947040Notes

Reaction equation

HRID 1947040 reaction equation
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]1)C1C=CC=CC=1.[C:26](O)(=[O:28])[CH3:27]>CCO.[OH-].[OH-].[Pd+2]>[C:26]([O:18][C:15]([CH:12]1[CH2:11][CH2:10][CH:9]([NH2:8])[CH2:14][CH2:13]1)([CH3:16])[CH3:17])(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59401621HCID 59401621, compound

Product 1

HCID 69307251HCID 69307251, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

2-(4-Dibenzylamino-cyclohexyl)-propan-2-ol (15 g) in EtOH (300 mL, abs) was treated with Pd(OH)2 (12.5 g). Acetic acid (6.3 mL) was added, and H2 was added slowly over 4.5 h. The reaction mixture was allowed to stand, then was filtered through a glass frit, washed with EtOH, filtered through a second glass frit, and the solvent removed in vacuo. The product was dissolved in hexane, and the hexane removed in vacuo (×3). The product was then triturated with ether, and the resultant solid filtered. The filtrate was evaporated, the residue dissolved in EtOH and solvent removed in vacuo. The product was then triturated in ether and the product filtered. The solvent was removed from both solid portions to yield 2-(4-aminocyclohexyl)-propan-2-ol acetate (6.52 g).

Workup

  1. additionH2 was added slowly over 4.5 h
  2. filtrationwas filtered through a glass frit
  3. washwashed with EtOH
  4. filtrationfiltered through a second glass frit
  5. customthe solvent removed in vacuo
  6. dissolutionThe product was dissolved in hexane
  7. customthe hexane removed in vacuo (×3)
  8. customThe product was then triturated with ether
  9. filtrationthe resultant solid filtered
  10. customThe filtrate was evaporated
  11. dissolutionthe residue dissolved in EtOH
  12. customsolvent removed in vacuo
  13. customThe product was then triturated in ether
  14. filtrationthe product filtered
  15. customThe solvent was removed from both solid portions

Sources & evidence

ORD record
ord-1a27ed65dac84750bff7d85a3f3ee5ca
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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