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

HRID 592972Notes

Reaction equation

HRID 592972 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-b1f61be012234a348a5af34f82a30a2d
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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