Hydrochloric Acid → 2-methyl-1-{(1R,5S)-8-[2-(2-phenylmorpholin-2-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole trihydrochloride

HRID 272002Notes

Reaction equation

HRID 272002 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][C@H:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[O:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:36]=[CH:37][CH:38]=[CH:39][C:4]=2[N:3]=1.[ClH:40]>C(Cl)(Cl)Cl.O1CCOCC1>[ClH:40].[ClH:40].[ClH:40].[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][C@H:9]3[N:14]([CH2:15][CH2:16][C:17]4([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[O:22][CH2:21][CH2:20][NH:19][CH2:18]4)[C@H:12]([CH2:11][CH2:10]3)[CH2:13]2)[C:5]2[CH:36]=[CH:37][CH:38]=[CH:39][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59835967tert-butyl 2-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2-phenylmorpholine-4-carboxylate

Product 1

HCID 689336682-methyl-1-{(1R,5S)-8-[2-(2-phenylmorpholin-2-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole trihydrochloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 2-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2-phenylmorpholine-4-carboxylate (330 mg, 0.62 mmol) in 5 mL CHCl3 was added 0.8 mL of a solution of 4N HCl in dioxane. After stirring at room temperature for 2 h, another 3 mL 4N HCl in dioxane was added and the mixture was heated at 40° C. for 90 min. The solution was then evaporated and dried in vacuo to provide 2-methyl-1-{(1R,5S)-8-[2-(2-phenylmorpholin-2-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole trihydrochloride, which was used without further purification. ESI-MS 431 (M+H).

Workup

  1. temperaturethe mixture was heated at 40° C. for 90 min
  2. customThe solution was then evaporated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9bd1a45d4fdb458991feebf731f742ec
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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