HCID 67214906, compound → (3aS,7aS)-1-[1-(4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one

HRID 2421053Notes

Reaction equation

HRID 2421053 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[CH:5]2[CH2:26][CH2:27][CH2:28][CH2:29][CH:4]2[NH:3]1>Cl.O1CCOCC1.O>[NH:16]1[CH2:17][CH2:18][CH:13]([N:10]2[CH2:9][CH2:8][CH:7]([N:6]3[C@H:5]4[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:4]4[NH:3][C:2]3=[O:1])[CH2:12][CH2:11]2)[CH2:14][CH2:15]1

Participants

5

Reactant 1

HCID 67214906HCID 67214906, compound

Product 1

HCID 24882730(3aS,7aS)-1-[1-(4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-oneYield 77.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 4-(2-oxooctahydro-1H-benzimidazol-1-yl)-1,4′-bipiperidine-1′-carboxylate (1.2 g, 2.95 mmol) was dissolved in a mixture of 4M HCl in dioxane (15 mL) and water (5 mL). The mixture was stirred at rt for 1 hour then concentrated in vacuo to provide the title compound as a white solid (0.7 g). 1H NMR (400 MHz, CHLOROFORM-D) free base: δ ppm 1.22-1.53 (m, 5H), 1.49-1.69 (m, 1H), 1.69-1.88 (m, 7H), 1.94 (m, 1H), 2.04-2.52 (m, 6H), 2.60 (t, J=11.33 Hz, 2H), 2.82-3.09 (m, 4H), 3.17 (d, J=12.89 Hz, 2H), 3.59-3.88 (m, 1H), 4.47-4.68 (m, 1H). MS (M+1): 307.3.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-8342f92859f94f86a3facd5ce310b369
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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