Water → Benzyl 4-bromopiperidine-1-carboxylate

HRID 1269768

Reaction equation

HRID 1269768 reaction equation
Br.[Br:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH2:9]([O:16][C:17](ON1C(=O)CCC1=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCOCC1.O>O1CCCC1>[Br:2][CH:3]1[CH2:8][CH2:7][N:6]([C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 83172Benzyl succinimido carbonateHCID 27346764-Bromopiperidine Hydrobromide

Product 1

HCID 2776275Benzyl 4-bromopiperidine-1-carboxylateYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromopiperidine hydrobromide (3.0 g, 12.2 mmol) in tetrahydrofuran (30 ml) were added 1-{[(benzyloxy)carbonyl]oxy}-2,5-pyrrolidinedione (3.20 g, 12.9 mmol), N-methylmorpholine (1.62 ml, 14.7 mmol) and 4-N,N-dimethylaminopyridine (30 mg) at room temperature, and stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a 1N-aqueous hydrochloric acid solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain benzyl 4-bromo-1-piperidinecarboxylate (3.58 g, 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a 1N-aqueous hydrochloric acid solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-8ffc2216144248a1b5320f2e36839be0
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Linked notes

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