Imidazole → HCID 58994589, compound

HRID 1190225Notes

Reaction equation

HRID 1190225 reaction equation
Br.[N+:2]([C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[C:26]([Si:30]([CH3:32])([CH3:31])[O:18][CH2:17][CH2:16][N:13]1[CH2:12][CH2:11][N:10]([CH2:9][C:8]2[CH:19]=[CH:20][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:15][CH2:14]1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12362121HCID 12362121, compound

Product 1

HCID 58994589HCID 58994589, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-[4-(4-nitro-benzyl)-piperazin-1-yl]-ethanol hydrobromide (as prepared in the previous step, 1.00 g, 2.89 mmol) in DMF (3 mL) was treated with imidazole (688 mg, 10.1 mmol) and tert-butyl-chloro-dimethyl-silane (566 mg, 3.76 mmol) at RT for 3 h. The mixture was partitioned between EtOAc (50 mL) and brine (50 mL), and the layers were separated. The organic layer was washed with brine (3×40 mL). The combined aqueous layers were extracted with EtOAc (1×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification of the residue on a 50-g Isolute SPE column on a FlashMaster system with 50% EtOAc-hexane afforded the title compound (1.03 g, 94%) as a pale yellow oil which solidified upon standing. Mass spectrum (ESI, m/z): Calcd. for C19H33N3O3Si, 380.2 (M+H). found 380.2.

Workup

  1. customThe mixture was partitioned between EtOAc (50 mL) and brine (50 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with brine (3×40 mL)
  4. extractionThe combined aqueous layers were extracted with EtOAc (1×50 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue on a 50-g Isolute SPE column on a FlashMaster system with 50% EtOAc-hexane

Sources & evidence

ORD record
ord-fbfdcf6ea2a74b8b9265fc0cbd5e23a0
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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