Sodium Bicarbonate → 4-(2-Fluoro-4-methylbenzyl)-1-(2-(4-hydroxyphenoxy)ethyl)piperidine hydrochloride

HRID 1955200Notes

Reaction equation

HRID 1955200 reaction equation
[ClH:1].[F:2][C:3]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[OH:17][C:18]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24]Br)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>>[ClH:1].[F:2][C:3]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:24][CH2:23][O:22][C:21]2[CH:26]=[CH:27][C:18]([OH:17])=[CH:19][CH:20]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 128339324-(2-Bromoethoxy)phenolHCID 232943474-(2-Fluoro-4-methylbenzyl)piperidine hydrochloride

Product 1

HCID 232945294-(2-Fluoro-4-methylbenzyl)-1-(2-(4-hydroxyphenoxy)ethyl)piperidine hydrochloride

Procedure

The title compound was prepared from 4-(2-fluoro-4-methylbenzyl)piperidine hydrochloride (375 mg, 1.54 mmol), 2-(4-hydroxyphenoxy)ethyl bromide (352 mg, 1.62 mmol) and NaHCO3 (265 mg, 3.16 mmol) as a near colorless powder (430 mg): mp 164-165° C.; 1H NMR (CD3OD) 1.51-1.70 (m, 2H), 1.84-2.00 (m, 3H), 2.31 (s, 3H), 2.63 (d, J=5.7 Hz, 2H), 2.94-3.12 (m, 2H), 3.44-3.70 (m, 4H), 4.26 (t, J=4.8 Hz, 2H), 6.74 (d, J=9.3 Hz, 2H), 6.82-6.96 (m, 4H), 7.07-7.14 (m, 1H); Anal. Calcd for C21H27ClFNO2 : C, 66.39; H. 7.16; N, 3.69. Found: C, 66.62; H, 6.99; N, 3.54.

Sources & evidence

ORD record
ord-d82d99c7678144db8cffd73d0c0edab5
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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