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Imidazole → Tert-butyl 4-(1H-imidazol-1-YL)piperidine-1-carboxylate

HRID 392501
Notes
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Reaction equation

HRID 392501 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 22662911Tert-butyl 4-(1H-imidazol-1-YL)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of the title compound from Step B (4.0 g, 14.32 mmoles) in DMF (120 mL) was added to a stirred solution of NaH (0.52 g, 21.66 mmoles) and imidazole (1.46 g, 21.47 mmoles) in DMF (20 mL) under nitrogen atmosphere. The mixture was stirred at 60° C. for 16 h. DMF was evaporated in vacuo. The resulting crude product was extracted with CH2Cl2 and the extract was successively washed with water and brine, and the CH2Cl2 was evaporated to leave the title residue which was chromatographed on silica gel using 3% (10% cone NH4OH in methanol)-CH2Cl2 as eluant to give the title compound (0.94 g, 26%). FABMS (M+1)=252; δH (CDCl3) 1.4 (s, 9H), 1.6-1.8 (m, 2H), 2.0 (dd, 2H), 2.8 (dt, 2H), 4.05 (m, 1H), 4.2 m, 2H), 6.9 (s, 1H), 7.0 (s, 1H), 7.65 (s, 1H).

Workup

  1. customDMF was evaporated in vacuo
  2. extractionThe resulting crude product was extracted with CH2Cl2
  3. washthe extract was successively washed with water and brine
  4. customthe CH2Cl2 was evaporated

Sources & evidence

ORD record
ord-bb3160eb51e34cf0ad408352b27c3d74
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800636B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes