Hydrochloric Acid → N-methyl(1-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2,3-dihydro-1H-inden-1-yl)methanamine

HRID 733445Notes

Reaction equation

HRID 733445 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1([CH2:20][CH2:21][N:22]2[C@H:27]3[CH2:28][CH2:29][C@@H:23]2[CH2:24][CH:25]([N:30]2[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=[C:31]2[CH3:39])[CH2:26]3)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)C(=O)OC(C)(C)C.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.O1CCOCC1>[CH3:1][NH:2][CH2:10][C:11]1([CH2:20][CH2:21][N:22]2[C@H:27]3[CH2:28][CH2:29][C@@H:23]2[CH2:24][CH:25]([N:30]2[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=[C:31]2[CH3:39])[CH2:26]3)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57679184HCID 57679184, compound

Product 1

HCID 57679157N-methyl(1-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2,3-dihydro-1H-inden-1-yl)methanamineYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl methyl[(1-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2,3-dihydro-1H-inden-1-yl)methyl]carbamate (0.7425 g, 1.404 mmole) was dissolved in 2 ml of DCM and 2 ml of 4M HCl in dioxane. After stirring the reaction was neutralized with saturated NaHCO3 and extracted with Et2O to afford N-methyl(1-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-2,3-dihydro-1H-inden-1-yl)methanamine (0.21 g, 35% yield).

Workup

  1. extractionextracted with Et2O

Sources & evidence

ORD record
ord-01d1ef4e0ee14040ab0e38d191542618
Source dataset
uspto-grants-2009_09
Patent number
US07589204B2

Reaction notes

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