1,1'-Carbonyldiimidazole → HCID 178451787, compound

HRID 1842492Notes

Reaction equation

HRID 1842492 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[NH2:38])[C:33]#[N:34]>CN(C=O)C.N1C=CC=CC=1>[C:33]([C:32]1[CH:35]=[CH:36][C:37]2[NH:38][C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)=[N:29][C:30]=2[CH:31]=1)#[N:34]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 178451787HCID 178451787, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (15 g, 65.5 mmol) in DMF (50 mL) and pyridine (50 mL) was added CDI (10.6 g, 65.5 mmol) at 45° C. and the mixture was stirred for another 2 h at this temperature. Then 3,4-diamino-benzonitrile (8.7 g, 65.5 mmol) was added and the mixture was stirred at RT overnight. Solvents were removed in vacuo and the residue was dissolved in HOAc (20 mL) and heated for 1 h at 100° C. Then the reaction mixture was concentrated and the residue was partitioned between DCM and aqueous of Na2CO3. The organic layer was dried over Na2SO4 and concentrated to give the crude product which was purified by column chromatography (ethyl acetate:petroleum ether=1:2) to give the compound tert-butyl 4-(5-cyano-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate (8 g, 65%) as pale solid.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customSolvents were removed in vacuo
  3. dissolutionthe residue was dissolved in HOAc (20 mL)
  4. concentrationThen the reaction mixture was concentrated
  5. customthe residue was partitioned between DCM and aqueous of Na2CO3
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified by column chromatography (ethyl acetate:petroleum ether=1:2)

Sources & evidence

ORD record
ord-d2c1268e0557490ab20dbf72512dc817
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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