Hydrochloric Acid → HCID 9800603, compound

HRID 2105253Notes

Reaction equation

HRID 2105253 reaction equation
[ClH:1].CC([CH:6]1[CH2:11][CH:10]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:17][CH:16]=2)=[O:13])[CH2:9][CH2:8][N:7]1C([O-])=O)(C)C.[OH-].[Na+]>CCOC(C)=O>[ClH:1].[CH2:25]([CH:22]([CH2:23][CH3:24])[CH:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]([CH:10]2[CH2:9][CH2:8][NH:7][CH2:6][CH2:11]2)=[O:13])=[CH:16][CH:17]=1)[N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86760939HCID 86760939, 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-dimethylethyl4-[[[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-350468a5c8224bbc96d97045ac2aef59
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

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