1,1'-Carbonyldiimidazole → HCID 10550636, compound

HRID 2289560Notes

Reaction equation

HRID 2289560 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:19][CH2:18][CH:14]([C:15]([OH:17])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>O1CCCC1.ClCCl>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:15]([CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:19][CH2:18]2)=[O:17])[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Product 1

HCID 10550636HCID 10550636, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of N-benzyloxycarbonyl isonipecotic acid (123.64 g) in tetrahydrofuran (300 ml) at 0° C. was added a solution of carbonyldiimidazole (68.80 g) in tetrahydrofuran (500 ml) and dichloromethane (300 ml). The resulting solution was stirred at ambient temperature for 2 hours. This solution was cooled to 0° C. and a solution of 1-(tert-butoxycarbonyl)piperazine (87.02 g) in tetrahydrofuran (200 ml) added dropwise over 20 minutes. The suspension obtained was stirred at ambient temperature for 48 hours. Solvent was evaporated. The residue was dissolved in diethyl ether/dichloromethane (1500 ml) and washed with water, 2M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution, dried (Na2SO4) and evaporated to give 1-(tert-butoxycarbonyl)-4-[1-(benzyloxycarbonyl)4-piperidylcarbonyl]piperazine (180.00 g) as a solid.

Workup

  1. temperatureThis solution was cooled to 0° C.
  2. customThe suspension obtained
  3. stirringwas stirred at ambient temperature for 48 hours
  4. customSolvent was evaporated
  5. dissolutionThe residue was dissolved in diethyl ether/dichloromethane (1500 ml)
  6. washwashed with water, 2M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-b1d66fdee27d4eec8e2d1cfa716c4aa2
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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