Piperidine → HCID 66722872, compound

HRID 505705Notes

Reaction equation

HRID 505705 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.[O:16]1[CH2:21][CH2:20][CH:19]([CH:22]=O)[CH2:18][CH2:17]1.N1CCCCC1>CO.C(OCC)(=O)C>[O:1]=[C:2]1[C:11](=[CH:22][CH:19]2[CH2:20][CH2:21][O:16][CH2:17][CH2:18]2)[CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 8082PiperidineHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 66722872HCID 66722872, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (2.9 mmol), tetrahydro-pyran-4-carbaldehyde (3.2 mmol), and piperidine (3.2 mmol) in 6 mL of methanol was heated to 65° C. overnight. The cooled mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel, eluting with ethyl acetate in hexane from 10% to 40%, to give 430 mg of the desired product. ES-MS m/z 301 (M+H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel
  5. washeluting with ethyl acetate in hexane from 10% to 40%

Sources & evidence

ORD record
ord-11a7dbd172134b8f9c2ff50c8442dd79
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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