1,1'-Carbonyldiimidazole → HCID 18919766, compound

HRID 1291075Notes

Reaction equation

HRID 1291075 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:25]([N:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH:35]2[CH2:34][CH2:33][N:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:37][CH2:36]2)=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 784611-Benzylpiperidin-4-olHCID 5204885-Nitropicolinic acid

Product 1

HCID 18919766HCID 18919766, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (0.03 mol) of 5-nitro-picolinic acid (Pharmazie 38 (1983), p. 593) and 4.87 g (0.03 mol) of carbonyidiimidazole were dissolved in 250 ml of THF and stirred at 60° for 3 hours. The mixture was subsequently treated with 5.75 g (0.03 mol) of 1-benzyl-4-hydroxy-piperidine, stirred at 0°-5° for 18 hrs., at room temperature for 3 hrs. and subsequently at 40° for 2 hrs. The reaction mixture was completely freed from solvent and the residue was chromatographed over neutral Alox (grade II) with dichloromethane as the eluent and recrystallized from ethyl acetate. 4.2 g (41%) of 1-benzyl-piperidin-4-yl 5-nitro-picolinate were obtained as yellow crystals; m.p. 175°-176°.

Workup

  1. stirringstirred at 0°-5° for 18 hrs
  2. wait, at room temperature for 3 hrs
  3. waitand subsequently at 40° for 2 hrs
  4. customthe residue was chromatographed over neutral Alox (grade II) with dichloromethane as the eluent
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1b63e3b824e04c0b9500698a1433a55d
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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