Potassium Carbonate → 2-Benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine Hydrobromide

HRID 1861749Notes

Reaction equation

HRID 1861749 reaction equation
[BrH:1].[CH2:2]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C(C1CCCCN1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:1][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.[BrH:1].[CH2:2]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 173898172-Benzylpiperidine hydrochlorideHCID 186215792-Benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine Hydrobromide

Product 2

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneHCID 186215792-Benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine HydrobromideYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine hydrobromide. From a mixture of 2-benzylpiperidine hydrochloride (1.00 g, 4.72 mmol), K2CO3 (1.30 g, 9.44 mmol) and 1-bromo-2-(4-nitrophenoxy)ethane (1.17 g, 4.96 mmol) in CH3CN (50 mL) there was obtained the hydrobromide as a pale yellow solid (888 mg, 45%); mp 180-182° C., 1H NMR (CDCl3) 1.35-2.42 (m, 6H), 2.75-405 (m, 7H), 4.50-4.95 (m, 2H), 6.95-7.37 (m, 7H), 8.15-8.26 (m, 2H), 11.72 and 11.88 (overlapping bs, 1H). Anal. Calcd for C20H25BrN2O3: C, 57.01; H, 5.98: N, 6.65. Found: C, 57.16; H, 6.01; N, 6.61.

Sources & evidence

ORD record
ord-43c4fcb475eb4b82a010b909d5a06a2e
Source dataset
uspto-grants-2003_03
Patent number
US06534525B1

Reaction notes

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