4-Benzylpiperidine → HCID 23294266, compound

HRID 1955239Notes

Reaction equation

HRID 1955239 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[O:18][CH2:19][CH2:20]Br>C1(C)C=CC=CC=1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:20][CH2:19][O:18][C:17]2[CH:22]=[CH:23][C:24]([N+:25]([O-:27])=[O:26])=[C:15]([OH:14])[CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 317384-BenzylpiperidineHCID 23294435HCID 23294435, compound

Product 1

HCID 23294266HCID 23294266, compoundYield 93,110%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

From a mixture of 4-benzylpiperidine (820 mg, 4.68 mmol), 2-(3-hydroxy-4-nitrophenoxy)ethyl bromide (556 g, 2.26 mmol) and KI (180 mg) in toluene (25 mL) was obtained 750 g (97%) of 4-benzyl-1-(2-(3-hydroxy-4-nitrophenoxy)ethyl)piperidine as a yellow powder, mp. 136-7° C. 1H NMR (CDCl3): 1.28-1.40 (m, 2H), 1.50-1.68 (m, 1H), 2.02-2.10 (m, 2H), 2.545 (d, 2H, J=7), 2.792 (t, 2H, J=6), 2.93-2.97 (m, 2H), 4.151 (t, 2H, J=6), 6.50-6.53 (m, 2H), 7.13-7.31 (m, 5H), 8.027 (d, 1H, J=10).

Sources & evidence

ORD record
ord-c88008db7b31459b81fe81edc5be269d
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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