Hydrochloric Acid → HCID 9800603, compound

HRID 429858Notes

Reaction equation

HRID 429858 reaction equation
[ClH:1].[CH2:2]([CH:4]([CH2:33][CH3:34])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[O:19])=[CH:13][CH:12]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)[CH3:3].[OH-].[Na+]>CCOC(C)=O>[ClH:1].[CH2:33]([CH:4]([CH2:2][CH3:3])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([CH:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)=[O:19])=[CH:13][CH:12]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22335531HCID 22335531, compound

Product 1

HCID 9800603HCID 9800603, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl conc. (3.6 ml) was added at RT to a mixture of (±)-1,1-dimethylethyl 4-[[[4-[2-ethyl-1-(1H-imidazol-1-yl)butyl]phenyl]amino]carbonyl]-1-piperidinecarboxylate (0.0032 mol) in EtOAc (30 ml). The mixture was stirred at RT for 4 hours, then basified with a concentrated NaOH solution and extracted with EtOAc and then CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue (1 g) was converted into the hydrochloric acid salt (1:1) in 2-propanol. The precipitate was filtered off and dried, yielding 0.85 g (68%) (±)-N-[4-[2-ethyl-1-(1H-imidazol-1-yl)butyl]-phenyl]-4-piperidinecarboxamide monohydrochloride (compound 57).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-4ab104b152d04f45b31b38ba4dadd539
Source dataset
uspto-grants-2001_11
Patent number
US06319939B1

Reaction notes

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