p-Toluenesulfonic acid → HCID 21717544, compound

HRID 548621Notes

Reaction equation

HRID 548621 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:18]1[CH2:19][CH2:20][N:15]([C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH:10]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 21717544HCID 21717544, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of tert-butyl-4-oxo-1-piperidine carboxylate (8.0 g, 40 mmol) and morpholine (3.6 g, 42 mmol) in benzene (16 mL) was added p-toluenesulfonic acid (40 mg) and the resulting solution was refluxed using a Dean-Stark trap for 24 h. After cooling to rt, the solution was concentrated under vacuum to afford the title compound a as a thick reddish-orange oil which was used without any further purification (11.1 g, ˜quant). 1H NMR (400 MHz, CDCl3): δ 7.36 (s, 1H), 3.94 (br s, 2H), 3.74 (m, 4H), 3.54 (m, 2H), 2.80 (m, 4H), 2.16 (br s, 2H), 1.47 (s, 9H).

Workup

  1. temperaturethe resulting solution was refluxed
  2. customfor 24 h
  3. concentrationthe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-4f02bc285d2f46ffb02a204a42445627
Source dataset
uspto-grants-2011_05
Patent number
US07943617B2

Reaction notes

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