Hydrochloric Acid → 4-(4-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine trihydrochloride

HRID 2088896Notes

Reaction equation

HRID 2088896 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[N:5]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=1.[Cl:27]CCl.[ClH:30].O1CCOCC1>CO>[ClH:27].[ClH:30].[ClH:27].[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[N:5]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 67112012tert-Butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 671132564-(4-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine trihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine tert-butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (0.80 g, 1.87 mmol), dichloromethane (20 mL), methanol (8 mL), and 4M hydrochloric acid in dioxane (9.36 mL, 20.0 eq) under nitrogen and let stir at room temperature. After 1.5 hours, concentrate in vacuo to give the title compound (0.82 g, 100%). MS (ES) m/z=327 [M]+.

Workup

  1. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b00fd3d1503b4ac1aa0b06e862cffb3c
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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