1,1'-Carbonyldiimidazole → 1-(1H-benzo[d]imidazol-6-yl)-5-(1-phenylpiperidin-4-yl)imidazolidin-2-one

HRID 706309Notes

Reaction equation

HRID 706309 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[C:11]1([N:17]2[CH2:22][CH2:21][CH:20]([CH:23]=O)[CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Si](C#N)(C)(C)C.[N:31]1([C:36](N2C=CN=C2)=[O:37])C=CN=[CH:32]1>[Pd]>[NH:3]1[C:4]2[CH:9]=[C:8]([N:10]3[CH:23]([CH:20]4[CH2:19][CH2:18][N:17]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[CH2:22][CH2:21]4)[CH2:32][NH:31][C:36]3=[O:37])[CH:7]=[CH:6][C:5]=2[N:1]=[CH:2]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 138429921-Phenylpiperidine-4-carbaldehydeHCID 178507353HCID 178507353, compound

Product 1

HCID 582290751-(1H-benzo[d]imidazol-6-yl)-5-(1-phenylpiperidin-4-yl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound was synthesized starting from 1H-benzo[d]imidazol-5-amine (0.400 g, 3 mmol), 1-phenylpiperidine-4-carbaldehyde (0.570 g, 3 mmol), TMSCN (0.375 mL, 3 mmol), Pd/C (10%, 0.02 g), TEA 1.05 mL, 7.5 mmol), di-(imidazol-1-yl)methanone (0.730 g, 4.5 mmol) as described in method 2.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-609b5e876eeb409fbe188076dcb968b6
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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