Ammonium Chloride → 4-(2-Methoxyethyl)piperidine

HRID 1282009Notes

Reaction equation

HRID 1282009 reaction equation
[CH3:1]C(C)([O-])C.[K+].C[C:8](P(OC)(O)=O)([C:10]([O-:12])=O)[CH3:9].C(OC([N:25]1[CH2:30][CH2:29]C(=O)[CH2:27][CH2:26]1)=O)(C)(C)C.[NH4+].[Cl-]>C1COCC1>[CH3:1][O:12][CH2:10][CH2:8][CH:9]1[CH2:29][CH2:30][NH:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 151727544-(2-Methoxyethyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

8.4 g (74.9 mmol) of potassium t-butoxide were suspended in 200 mL of THF. To this mixture at rt was slowly added a solution of 13.7 g (75.4 mmol) of trimethylphosphonoacetate in 20 mL of THF. After stirring for 30 min, a solution of 10 g (50.2 mmol) of 1-t-butoxycarbonyl-4-piperidone in 50 mL of THF was added and the mixture was heated to 60° C. for 3.5 h. To the reaction mixture was added 250 mL of a sat'd aqueous NH4Cl solution and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. Chromatography on silica eluting with hexane:ethyl acetate=4:1 gave the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e42f1140032f4b3295c4fa7cf078d902
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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