Benzoyl chloride → Ethyl 1-benzoyl-3-piperidinecarboxylate

HRID 432789

Reaction equation

HRID 432789 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.C(N(C(C)C)CC)(C)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[C:21]([N:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 98969Ethyl nipecotate

Product 1

HCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylateYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Commercially available ethyl nipecotate (1.48 ml; 9.53 mmol) was dissolved in dichloromethane (20 ml), and diisopropylethylamine (1.82 ml; 10.45 mmol) was added. Benzoyl chloride (1.1 ml; 9.53 mmol) was then added slowly to control any rise in reaction temperature. After addition was complete the mixture was allowed to stir at ambient temperature for approximately 1-4 hours. The mixture was then diluted with fresh dichloromethane and washed with 1 N HCl. The dichloromethane solution was dried with anhydrous potassium carbonate and evaporated at ambient temperature under reduced pressure. The crude material was purified by high-vacuum distillation at approximately 200° C./0.1 torr giving ethyl 1-benzoyl-3-piperidinecarboxylate (2.38 g) as a colorless oil. (The temperatures given for distillations in these examples are oven temperatures and represent approximations. Similarly, the vacuum levels given for distillations are also approximates.) MS m/z (positive ion) 545 (dimer+; 25), 284 (M+Na+; 90), 262 (MH+; 100), 216 (25).

Workup

  1. customin reaction temperature
  2. additionAfter addition
  3. washwashed with 1 N HCl
  4. dry with materialThe dichloromethane solution was dried with anhydrous potassium carbonate
  5. customevaporated at ambient temperature under reduced pressure
  6. distillationThe crude material was purified by high-vacuum distillation at approximately 200° C./0.1 torr

Sources & evidence

ORD record
ord-aa11302365da476296f1ec8e31b39aa9
Source dataset
uspto-grants-2003_12
Patent number
US06664271B1

Linked notes

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