4-Benzylpiperidine → 4-Benzyl-1-(2-(4-benzyloxy-3-nitrophenoxy)ethyl)piperidine

HRID 1955237Notes

Reaction equation

HRID 1955237 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.[CH2:14]([O:21][C:22]1[CH:31]=[CH:30][C:25]([O:26][CH2:27][CH2:28]Br)=[CH:24][C:23]=1[N+:32]([O-:34])=[O:33])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:28][CH2:27][O:26][C:25]2[CH:30]=[CH:31][C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:23]([N+:32]([O-:34])=[O:33])[CH:24]=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 232944042-(4-Benzyloxy-3-nitrophenoxy)ethyl bromide

Product 1

HCID 232944524-Benzyl-1-(2-(4-benzyloxy-3-nitrophenoxy)ethyl)piperidineYield 77.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

From a mixture of 4-benzylpiperidine (2.68 9, 15.1 mmol), 2-(4-benzyloxy-3-nitrophenoxy)ethyl bromide (2.65 g, 7.52 mmol) and KI (110 mg) in toluene (25 mL) was obtained 2.59 g (77%) of 4-benzyl-1-(2-(4-benzyloxy-3-nitrophenoxy)ethyl)piperidine as an orange-yellow oil. 1H NMR (CDCl3): 1.30-1.42 (m, 2H), 1.50-1.60 (m, 1H), 1.64-1.68 (m, 2H), 2.02-2.10 (m, 2H), 2.547 (d, 2H, J=7), 2.777 (t, 2H, T=6), 2.95-3.00 (m, 2H), 4.085 (t, 2H, J=6), 5.181 (s, 2H), 7.02-7.46 (m, 8H).

Sources & evidence

ORD record
ord-015a2e03db4545e89522ea4ccdaea661
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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