Hydrochloric Acid → 4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2047372Notes

Reaction equation

HRID 2047372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[NH:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:31]I.Cl>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]([CH3:31])[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 595680504-[3-(1H-Benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 595682004-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[3-(1H-benzoimidazol-2-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (0.83 g, 2.20 mmol) (obtained as described in method B) and NaH 60% oil (0.11 g, 4.39 mmol) in THF (10 mL) was stirred at room temperature for 1 h. Methyl iodide (0.27 mL, 4.39 mmol) was added and the resulting solution was stirred overnight. Water (15 mL) was added to the reaction solution, then the suspension was neutralized with 1N HCl and extracted with EtOAc (3×40 mL) The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was triturated with Et2O and the solid obtained filtered, to give 0.76 g (88%) of the title compound.

Workup

  1. stirringthe resulting solution was stirred overnight
  2. extractionextracted with EtOAc (3×40 mL) The combined organic layers
  3. dry with materialwere dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with Et2O
  7. customthe solid obtained
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1fb32b10416c44fa9d6d8c1bbd9418f4
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

Loading…