Potassium Carbonate → HCID 23084249, compound

HRID 1162332Notes

Reaction equation

HRID 1162332 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:22])=[C:5]([CH2:7][NH:8][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)[N:6]=1.C1CCN2C(=NCCC2)CC1.[C:34](=O)([O-])[O-:35].[K+].[K+]>ClCCl>[CH3:1][C:2]1[N:6]2[C:34](=[O:35])[N:8]([CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]3)[CH2:7][C:5]2=[C:4]([CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23138170tert-butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylate

Product 1

HCID 23084249HCID 23084249, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylate (8.0 g) obtained in Example 88a) was dissolved in dichloromethane (100 ml), DBU (3.6 ml) and N,N′-carbonyldiimidazole (3.9 g) were added thereto. The reaction solution was mixed for 15 hours, and then the reaction solution was poured into an aqueous potassium carbonate solution and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and then the residue was purified with silica gel column to obtain a pale yellow oily title compound (7.8 g, 97%).

Workup

  1. additionThe reaction solution was mixed for 15 hours
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified with silica gel column

Sources & evidence

ORD record
ord-791240d623194cfd87356eb57f1a516e
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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