N-bromobutanimide → HCID 178451789, compound

HRID 2283939Notes

Reaction equation

HRID 2283939 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C1C(=O)N([Br:26])C(=O)C1>C1COCC1>[Br:26][C:5]1[N:1]=[C:2]([CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[NH:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 17840015tert-butyl 4-(1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 178451789HCID 178451789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-(1H-imidazol-2-yl)piperidine-1-carboxylate (20.04 g, 79.74 mmol) in THF (450 mL) was cooled to −46 C (bath) before the flask was charged with NBS (14.27 g) in equal portions (10-min apart). LCMS data indicated complete reaction after 15 min, so the contents were concentrated to a yellow, solid foam that was further dried under vacuum overnight. The crude material (monobromide:dibromide=40:27) was purified by chromatography to give pure white solid (8.08 g, 24.47 mmol, 31%) as the title compound.

Workup

  1. customreaction after 15 min
  2. concentrationso the contents were concentrated to a yellow, solid foam that
  3. customwas further dried under vacuum overnight
  4. customThe crude material (monobromide:dibromide=40:27) was purified by chromatography

Sources & evidence

ORD record
ord-401ce3161fb149d89860472d7f592bf5
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

Loading…