HCID 18969307, compound → 1,1-Dimethylethyl 4-(4-amino-1H-imidazol-1-yl)-1-piperidinecarboxylate

HRID 1411909Notes

Reaction equation

HRID 1411909 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:8]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[N:5]=[CH:6][N:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:8]=1

Participants

4

Reactant 1

HCID 18969307HCID 18969307, compound

Product 1

HCID 189693351,1-Dimethylethyl 4-(4-amino-1H-imidazol-1-yl)-1-piperidinecarboxylateYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask was purged with nitrogen and charged with 243b (2.3 g, 7.8 mmol), 10% palladium on carbon (10% wet, 230 mg), and ethanol (40 mL). The mixture was evacuated, charged with hydrogen gas, and stirred at room temperature for 3 h. The hydrogen was then evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 243c (2.0 g, 95%). MS-ESI: [M+H]+ 267.2.

Workup

  1. customA 100-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe mixture was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-498309d4841649fbb3e23e188151f168
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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