4-(2-Bromoethoxy)phenol → 4-(1-Adamantylmethyl)-1-(2-(4-hydroxyphenoxy)ethyl)piperidine

HRID 324560Notes

Reaction equation

HRID 324560 reaction equation
Cl.[C:2]12([CH2:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[OH:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]Br)=[CH:22][CH:21]=1>>[C:2]12([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([CH2:26][CH2:25][O:24][C:23]4[CH:28]=[CH:29][C:20]([OH:19])=[CH:21][CH:22]=4)[CH2:15][CH2:14]3)[CH2:11][CH:6]3[CH2:5][CH:4]([CH2:10][CH:8]([CH2:7]3)[CH2:9]1)[CH2:3]2

Participants

3

Reactant 2

HCID 128339324-(2-Bromoethoxy)phenolHCID 186214804-(1-Adamantylmethyl)piperidine hydrochloride

Product 1

HCID 186214734-(1-Adamantylmethyl)-1-(2-(4-hydroxyphenoxy)ethyl)piperidine

Procedure

b)The title compound was prepared from 4-(1-adamantylmethyl)piperidine hydrochloride (350 mg, 1.30 mmol) and 2-(4-hydroxyphenoxy)ethyl bromide (295 mg, 1.36 mmol) as a beige crystalline solid (387 mg, 81%): mp 178-179° C.; 1H NMR (DMSO-d6) 0.93 (d, J=5.1, 2H), 1.05-1.70 (m, 17H), 1.85-2.07 (m, 5H), 2.56 (t, J=6.0, 2H), 2.72-2.88 (m, 2H), 3.90 (t, J=6.0, 2H), 6.63 (d, J=9.0, 2H), 6.71 (d, J=9.0, 2H), 8.88 (bs, 1H); Anal. calcd for C24H35NO2: C, 78.00; H, 9.55; N, 3.79. Found: C, 78.03; H, 9.44; N, 3.77.

Sources & evidence

ORD record
ord-857b2966a8894c48ad5ecd67f6221134
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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