Hydrochloric Acid → Tert-butyl 4-(2-pyrrolidin-1-ylacetyl)piperidinecarboxylate

HRID 2112756Notes

Reaction equation

HRID 2112756 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(N(CC)CC)C.Cl>O1CCCC1>[N:18]1([CH2:2][C:3]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)=[O:4])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31268PyrrolidineHCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Product 1

HCID 23079654Tert-butyl 4-(2-pyrrolidin-1-ylacetyl)piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 4-(2-bromoacetyl)piperidinecarboxylate (0.85 g, 2.8 mmol) was dissolved in tetrahydrofuran (8.5 mL), and the solution was mixed with pyrrolidine (0.46 mL, 5.6 mmol) and triethylamine (0.78 mL, 5.6 mmol) with stirring at room temperature, followed by stirring for twenty-four hours. The reaction mixture was mixed with diluted hydrochloric acid (0.5 mol/L, 27 mL) and washed with ethyl acetate. The aqueous layer was adjusted to be basic with an aqueous potassium hydroxide solution added under ice-cooling and was extracted with ethyl acetate. The organic layer was washed with brine, was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was dried under reduced pressure and thereby yielded tert-butyl 4-(2-pyrrolidin-1-ylacetyl)piperidinecarboxylate (0.72 g, 87%).

Workup

  1. stirringby stirring for twenty-four hours
  2. washwashed with ethyl acetate
  3. additionadded under ice-
  4. temperaturecooling
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-0b7613d799e14b7dafc3f1d1e201ea05
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

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