HCID 23294287, compound → HCID 23294376, compound

HRID 1955184Notes

Reaction equation

HRID 1955184 reaction equation
[BrH:1].[Cl:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1>CO.[Pd]>[BrH:1].[BrH:1].[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([Cl:2])=[CH:27][CH:26]=3)[CH2:13][CH2:12]2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 23294287HCID 23294287, compound

Product 1

HCID 23294376HCID 23294376, compoundYield 125.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-chlorobenzyl)-1-(2-(4-nitrophenoxy)ethyl)piperidine hydrobromide (500 mg, 1.10 mmol) and Pd/C (10%, 50 mg) in MeOH (25 mL) was shaken under H2 (20-30 psi, Parr) for 2.25 h and worked up to give a beige powder (350 mg, 63%): mp>130° C.; 1H NMR (DMSO-d6) 1.37-1.88 (m, 5 H), 2.45-3.75 (m, 8 H), 4.30-4.42 (m, 2 H), 7.04-7.38 (m, 8 H), 9.35-10.20 (m, 4 H); HRMS Calcd for C20H25ClN2O: 344.1655. Found: 344.1656.

Sources & evidence

ORD record
ord-f94769f448394a9f9f9cf47eb652bab2
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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