4-Bromophenol → 1-[2-(4-Bromophenoxy)ethyl]piperidine

HRID 1359147Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-bromophenol (5.2 g, 30 mmol), K2CO3 (10.4 g, 75 mmol) and anhydrous DMF (50 ml) were mixed together under Ar and heated at 100° C. 1-(2-chloroethyl)-piperidine hydrochloride (5.5 g, 30 mmol) was added in portions over 10 min and the reaction maintained at 100° C. for 1.5 h. After cooling the reaction, the solid was filtered off and the solvent removed under vacuum. The crude product was chromatographed on silica gel with methanol/ethyl acetate (3:1) to yield 6.7 g (78%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 1.44 (2H, m, NCH2CH2CH2), 1.59, (4H, m, NCH2CH2), 2.48 (4H, m, NCH2CH2), 2.73 (2H, t, NCH2CH2O), 4.03 (2H, t, NCH2CH2O), 6.76 (2H, d, ArH), 7.33 (2H, d, ArH).

Workup

temperaturethe reaction maintained at 100° C. for 1.5 h
temperatureAfter cooling
customthe reaction
filtrationthe solid was filtered off
customthe solvent removed under vacuum
customThe crude product was chromatographed on silica gel with methanol/ethyl acetate (3:1)

Sources & evidence

ORD record: ord-1d3033cc48574e9097b9dc60a5321418
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599921B2

Reaction notes

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