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Potassium Carbonate → 6-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde

HRID 445225
Notes
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Reaction equation

HRID 445225 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1[CH:14]=[O:15].[N:16]1([CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([O:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:26][CH:27]=1)=[C:3]([CH:14]=[O:15])[CH2:4][CH2:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106090214-[2-(Piperidin-1-yl)ethoxy]phenolHCID 112530501-Chloro-6-methoxy-3,4-dihydronaphthalene-2-carbaldehyde

Product 1

HCID 583385916-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehydeYield 122.4%

Reagents, catalysts & solvents 1

HCID 14284
4-(Dimethylamino)pyridine
Catalyst

Conditions

Temperature
100 °C

Procedure

To a 3-necked round bottom flask, add 1-chloro-6-methoxy-3,4-dihydronaphthalene-2-carbaldehyde (2.25 g, 10.1 mmol), 4-(2-(piperidin-1-yl)ethoxy)phenol (1.8 g, 8.24 mmol), tetra-N-butylammonium iodide (50 mg, 0.14 mmol), potassium carbonate (4.1 g, 29.8 mmol), and 4-dimethylaminopyridine (120 mg, 0.99 mmol). Purge the reaction vessel with nitrogen. Add dimethylformamide (30 mL) slowly to the reaction. Heat the mixture to 100° C. with stirring and hold for 4 hours. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times. Dry the combined organic layers over MgSO4, filter, and concentrate to give 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carbaldehyde (4.11 g).

Workup

  1. customPurge the reaction vessel with nitrogen
  2. customAdd dimethylformamide (30 mL) slowly to the reaction
  3. temperatureCool the reaction mixture to room temperature
  4. customquench with ice-water
  5. extractionExtract the mixture with ethyl acetate three times
  6. dry with materialDry the combined organic layers over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-665326ce43e44f6d9c6e57583f565fd5
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476300B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes