Hydrochloric Acid → HCID 67265100, compound

HRID 1685163Notes

Reaction equation

HRID 1685163 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[N:16]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:19]=2)([OH:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:33].CO>C(Cl)Cl>[ClH:27].[ClH:33].[Cl:27][C:22]1[CH:21]=[C:20]([C:18]2[N:19]=[C:15]([C:11]3([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:16]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH:17]=2)[CH:25]=[CH:24][C:23]=1[F:26]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 67264921HCID 67264921, compound

Product 1

HCID 67265100HCID 67265100, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-[4-(3-chloro-4-fluoro-phenyl)-1-(2-dimethylamino-ethyl)-1H-imidazol-2-yl]-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.00 equiv; 1.68 mmol; 785.00 mg) in 5 mL DCM and slowly add hydrogen chloride (24.00 mmol; 6.00 mL of 4M in dioxane) at RT. After 5 min, the solution becomes cloudy then an oily white solid comes out of solution. Add 2 mL methanol to get the solid back in solution. At 30 min, HPLC shows 25% starting material. Add 1 mL additional HCl solution. After total of 2 h stirring at RT, concentrate under vacuum. Re-dissolve in DCM and evaporate under vacuum to a white solid; Dry the white solid in a vacuum oven at 45° C. to 900 mg of the title compound. ES(MS): (m/z)=367.0 (M+H).

Workup

  1. customto get the solid back in solution
  2. waitAt 30 min
  3. concentrationconcentrate under vacuum
  4. customRe-dissolve in DCM and evaporate under vacuum to a white solid
  5. dry with materialDry the white solid in a vacuum oven at 45° C. to 900 mg of the title compound

Sources & evidence

ORD record
ord-432297f889294eeebe7c47ccd020b426
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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