Sodium hydride → (RS)-1-Benzyl-2-(4-phenyl-imidazol-1-ylmethyl)-piperidine

HRID 549345Notes

Reaction equation

HRID 549345 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][N:17]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:22]([N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[CH2:15][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 231462741-Benzyl-2-(bromomethyl)piperidineHCID 178418822HCID 178418822, compound

Product 1

HCID 67158353(RS)-1-Benzyl-2-(4-phenyl-imidazol-1-ylmethyl)-piperidineYield 24.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Phenylimidazole (1.3 g) was treated with sodium hydride (0.6 g 50% in oil) in dry tetrahydrofuran (80 ml). When gas evolution had ceased, 2-bromomethyl-N-benzylpiperidine (2.5 g) in tetrahydrofuran (30 ml) was added. The mixture was stirred for 16 h, solvent removed at reduced pressure and treated with ice/water (1:1, 100 ml). The mixture was extracted with dichloromethane (2×), the combined organic phase washed with water, solvent removed at reduced pressure and the residue column chromatographed (silica gel, 0.5→9.5% dichloromethane/methanol). Appropriate fractions were combined to give the title compound 0.72 g.

Workup

  1. customsolvent removed at reduced pressure
  2. additiontreated with ice/water (1:1, 100 ml)
  3. extractionThe mixture was extracted with dichloromethane (2×)
  4. washthe combined organic phase washed with water, solvent
  5. customremoved at reduced pressure
  6. customthe residue column chromatographed (silica gel, 0.5→9.5% dichloromethane/methanol)

Sources & evidence

ORD record
ord-e22d8e96d792488593984e213c098efe
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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