Triethylamine → 1-(2-(4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine

HRID 445227Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8](C(O)=O)[CH2:7][CH2:6]2.C(N(CC)CC)C.[Br:39]N1C(=O)CCC1=O>ClCCl>[Br:39][C:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a flask, add 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid (0.4 g, 0.68 mmol), dichloromethane (10 mL), and triethylamine (0.2 mL, 1.43 mmol). Stir the mixture at 25° C. for 10 min. Add N-Bromosuccinimide (0.5 g; 4.13 equiv; 2.81 mmol) in portions. 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 over MgSO4, filter, and concentrate to dryness to give 1-(2-(4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine as a yellow oil (300 mg).

Workup

temperatureCool the reaction mixture to room temperature
customquench with ice-water
extractionExtract the mixture with ethyl acetate three times
dry with materialDry the combined organic layers over MgSO4
filtrationfilter
concentrationconcentrate to dryness

Sources & evidence

ORD record: ord-ccbc0b2bbbfa487f86758f94b06783d5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476300B2

Reaction notes

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