Benzoyl chloride → Ethyl 1-benzoylpiperidine-4-carboxylate

HRID 617191Notes

Reaction equation

HRID 617191 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[C:19]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of ethyl isonipecotate (60 g, 0.382 mol) and triethylamine (38.65 g, 0.382 mol) in tetrahydrofuran (360 ml) was added dropwise benzoyl chloride (53.7 g, 0.382 mol) over a period of about 2 hours under nitrogen atmosphere. The reaction mixture was stirred for about 2 hours at the same temperature, and was filtered. The filtrate was evaporated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was dried over magnesium sulfate, and evaporated in vacuo. Crystallization from isopropyl alcohol gave the titled compound (90.9 g).

Workup

  1. filtrationwas filtered
  2. customThe filtrate was evaporated in vacuo
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customCrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-beb12353bd5c43178066c85127a8b49f
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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