Hydrochloric Acid → (3aS,7aS)-1-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one

HRID 1642485Notes

Reaction equation

HRID 1642485 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3([CH3:25])[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[CH2:9][CH2:8]2)[C@H:5]2[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:4]2[NH:3]1.Cl>O1CCOCC1>[CH3:25][C:13]1([N:10]2[CH2:11][CH2:12][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])[CH2:8][CH2:9]2)[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57619807Tert-butyl 3-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-1-yl]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate

Product 1

HCID 57619793(3aS,7aS)-1-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Tert-butyl 3-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-1-yl]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate (1.85 g, 4.55 mmol) in dioxane was added with 4N HCl solution in dioxane (11.4 mL, 45.5 mmol) and was stirred at room temperature under nitrogen atmosphere overnight. Then solvent was removed under reduced pressure to give the title compound as a white solid (1.3 g), which was used for the subsequent step without further purification. MS (M+1): 307.28.

Workup

  1. customThen solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-346797aef65d49b8a8d143497c2c8554
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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