1,1'-Carbonyldiimidazole → HCID 18919903, compound

HRID 1291076Notes

Reaction equation

HRID 1291076 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39](O)[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH:39]2[CH2:38][CH2:37][N:36]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:41][CH2:40]2)=[O:11])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 784611-Benzylpiperidin-4-olHCID 18919853HCID 18919853, compound

Product 1

HCID 18919903HCID 18919903, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 g (0.00043 mol) of 6-trifluoroacetamido-nicotinic acid was dissolved in 10 ml of THF, treated with 0.073 g (0.00045 mol) of carbonyldiimidazole and stirred at 60° for 2 hrs. Then, 0.086 g (0.00045 mol) of 1-benzyl-4-hydroxypiperidine was added and the mixture was stirred at 60° overnight. The reaction mixture was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.097 g (72%) of 1-benzyl-piperidin-4-yl 6-amino-nicotinate was obtained as white crystals; m.p. 135°-136°.

Workup

  1. stirringthe mixture was stirred at 60° overnight
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane (1:1) as the eluent

Sources & evidence

ORD record
ord-18ab0aa083e1489383f5a9361adc0c27
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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