2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(2-(4-(2-Bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine

HRID 445228Notes

Reaction equation

HRID 445228 reaction equation
[Br:1][C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(#N)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 583385381-(2-(4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine

Product 1

HCID 583385631-(2-(4-(2-Bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidineYield 27.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a round bottom flask, add 1-(2-(4-(2-bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine (6.7 g, 6.6 mmol) and acetonitrile (50 mL). Stir the mixture at 25° C. for 5 min. Add 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (3.2 g, 14.1 mmol) slowly to the reaction mixture. Heat the mixture to 80° C. and stir at the temperature for 14 hours. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times and discard the aqueous phase. Dry the combined organic layers (MgSO4), filter, and concentrate to dryness. Purify by flash chromatography to give 1-(2-(4-(2-bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine as a brown solid (817 mg). 1HNMR (d-DMSO, 300 MHZ): 7.68 (3H, m), 7.43 (1H, s), 7.15 (1H, m), 6.97 (2H, d), 6.72 (2H, d), 4.26 (2H, s), 3.85 (3H, s), 3.48 (4H, m), 2.96 (2H, m), 1.70 (6H, m).

Workup

  1. temperatureHeat the mixture to 80° C.
  2. stirringstir at the temperature for 14 hours
  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 (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate to dryness
  9. customPurify by flash chromatography

Sources & evidence

ORD record
ord-fed522ee1c354d17ac10ab97f995a778
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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