tert-Butyl 4-(3-carbamoylpropyl)piperidine-1-carboxylate → 4-(Piperidin-4-yl)butanamide

HRID 2376848Notes

Reaction equation

HRID 2376848 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)(=[O:3])[NH2:2]>FC(F)(F)C(O)=O>[NH:10]1[CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][CH2:4][C:1]([NH2:2])=[O:3])[CH2:8][CH2:9]1

Participants

3

Reactant 1

HCID 21949352tert-Butyl 4-(3-carbamoylpropyl)piperidine-1-carboxylate

Product 1

HCID 219492354-(Piperidin-4-yl)butanamideYield 230.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(3-carbamoylpropyl)piperidine-1-carboxylate (0.38 g, 1.4 mmol, Production example 44-1) was dissolved in trifluoroacetic acid (2 ml) and the reaction mixture was stirred at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure and then azeotropically distilled with toluene. The residue was partitioned between tetrahydrofuran and a saturated aqueous solution of sodium hydrogencarbonate; and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure; and the residue was purified by silica gel chromatography (Fuji Silysia NH, ethyl acetate-methanol system) to yield the title compound (0.55 g, quantitative) as pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationazeotropically distilled with toluene
  3. customThe residue was partitioned between tetrahydrofuran
  4. dry with materialand the organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customand the residue was purified by silica gel chromatography (Fuji Silysia NH, ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-521f21048bb84c4a8ae59f72a73e724a
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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