Piperidine → HCID 9824560, compound

HRID 1786535Notes

Reaction equation

HRID 1786535 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([Br:17])[C:14]=1[O:15][CH3:16])[CH:6]=[C:7]([C:10]#[N:11])[C:8]#[N:9].[C:18]1([OH:28])[C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.N1CCCCC1>C(O)C>[NH2:9][C:8]1[O:28][C:18]2[C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[CH:21]=[CH:20][C:19]=2[CH:6]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:14]([O:15][CH3:16])=[C:13]([Br:17])[CH:12]=2)[C:7]=1[C:10]#[N:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 3773318HCID 3773318, compound

Product 1

HCID 9824560HCID 9824560, compoundYield 1.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 3,4-dimethoxy-5-bromobenzylidenemalononitrile (293 mg, 1 mmol) and 5,6,7,8-Tetrahydro-1-naphthol (148 mg, 1 mmol) in ethanol (4 ml) was added piperidine (0.1 ml, 1 mmol), and the mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by column chromatography (EtOAc/Hexane, 1:2), yielding the title compound (6 mg, 1.4%). 1H NMR (CDCl3): 7.89 (d, J=2.0, 1H), 6.80-6.69 (m, 3H), 4.63 (s, 3H), 3.86 (s, 3H), 3.83 (s, 3H), 2.72 (m, 4H), 1.8 (m, 4H).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (EtOAc/Hexane, 1:2)

Sources & evidence

ORD record
ord-38a4490365184c17bf9ebd83390c64c8
Source dataset
uspto-grants-2009_03
Patent number
US07507762B2

Reaction notes

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