1-[2-(4-Benzyloxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride → 1-[2-(4-Hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride

HRID 1955195Notes

Reaction equation

HRID 1955195 reaction equation
[ClH:1].C([O:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:1].[OH:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[CH2:19][CH2:18]2)=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 700789441-[2-(4-Benzyloxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 700815991-[2-(4-Hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[2-(4-benzyloxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride (250 mg, 0.55 mmol) in 25 mL of ethanol with 60 mg of 20% Pd(OH)2 was hydrogenated at 30 psi of hydrogen to give 140 mg (88%) of the title compound, mp 198-200° C. 1H NMR (CD3OD) 1.6 (m, 2 H), 1.881-1.923 (m, 3 H), 2.288 (s, 3 H), 2.572 (d, J=6.6 Hz, 2 H), 3.06 (m, 2 H), 3.473 (m, 2 H), 3.61 (m, 2 H), 4.243 (t, J=5.1 Hz, 2 H), 6.709 (dd, J1 =2.4 Hz, J2 =6.6 Hz, 2 H), 6.830 (dd, J1 =2.4 Hz, J2 =6.6 Hz, 2 H), 7.703 (m, 4 H). Anal. Calcd for C21H28ClNO2.0.5H2O: C, 68.00; H, 7.88; N, 3.78. Found: C, 68.14; H, 7.65; N. 3.72.

Sources & evidence

ORD record
ord-3fa185ce40694d13bc6fda3631d6f093
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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