Triethylamine → Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylate

HRID 12396

Reaction equation

HRID 12396 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.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>ClCCl>[C:21]([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:22])[C:20]([CH3:25])([CH3:24])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 1164515Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl isonipecotate (20 mL, 130 mmol) was dissolved in 130 mL of dichloromethane and cooled to 0° C. and triethyl amine (19.9 mL, 143 mmol) was added. Trimethylacetyl chloride (16.8 mL, 136 mmol) was added dropwise and the reaction was allowed to warm to rt and stirred for 16 h. The reaction mixture was washed with hydrochloric acid solution (1.0 M, aq), sodium bicarbonate (sat., aq.) and sodium chloride (sat., aq.). The organic layer dried over magnesium sulfate, filtered and the solvent removed to provide 29.5 g (94%) of 20a as a pale orange liquid. LC-MS m/z 242 [M+H]+.

Workup

  1. temperatureto warm to rt
  2. washThe reaction mixture was washed with hydrochloric acid solution (1.0 M, aq), sodium bicarbonate (sat., aq.) and sodium chloride (sat., aq.)
  3. dry with materialThe organic layer dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-54295f7da89143368c391cc8da153b10
Source dataset
uspto-grants-2010_06
Patent number
US07728008B2

Linked notes

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