Hydrochloric Acid → HCID 178511526, compound

HRID 1600685Notes

Reaction equation

HRID 1600685 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][C:15](=[O:28])[N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1.[OH-].[Na+]>CO>[O:28]=[C:15]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)[CH2:14][C@H:11]1[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 178453926HCID 178453926, compound

Product 1

HCID 178511526HCID 178511526, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trans-{4-[2-oxo-2-(4-phenyl-piperazin-1-yl)-ethyl]-cylohexyl}-carbamic acid tert-butyl ester (18.1 g, 0.045 mol) was taken up in MeOH (275 mL) and treated with 4 M HCl in dioxane (56 mL, 0.224 mol) and allowed to stand 22 hours. Concentration to dryness yielded a solid which was treated with 2N NaOH (175 mL) and extracted with CH2Cl2. The extracts were washed with water, brine, and dried (Na2SO4). After evaporation of the solvent, the residue was crystallized in Et2O yielding trans-{4-[2-oxo-2-(4-phenyl-piperazin-1-yl)-ethyl]-cyclohexyl}-amine as a white solid, 11.2 g (83%); mp 90-93° C.

Workup

  1. concentrationConcentration to dryness
  2. customyielded a solid which
  3. extractionextracted with CH2Cl2
  4. washThe extracts were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of the solvent
  7. customthe residue was crystallized in Et2O

Sources & evidence

ORD record
ord-dc45d9192fa34acfb52568dc8719bf74
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

Loading…