Sodium Iodide → 1-(4-chlorobenzyl)-4-[N-(3,3-diphenylpropyl)aminomethyl]piperidine

HRID 279294Notes

Reaction equation

HRID 279294 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.CS(O[CH2:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)=O.[Na+].[I-]>>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:6]2[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][CH2:22][CH2:23][CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:4][CH2:5]2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 18426145{[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amineHCID 222382923,3-Diphenylpropyl methanesulfonate

Product 1

HCID 184261521-(4-chlorobenzyl)-4-[N-(3,3-diphenylpropyl)aminomethyl]piperidineYield 54%

Procedure

4-(Aminomethyl)-1-(4-chlorobenzyl)piperidine (120 mg) was alkylated with 3,3-diphenylpropyl methanesulfonate (1.0 equiv.) in the presence of NaI (2.6 equiv.) in CH2CN at 70° C. for 16 h. General workup and column chromatography (SiO2) afforded 1-(4-chlorobenzyl)-4-{N-(3,3-diphenylpropyl)aminomethyl}piperidine (118 mg, 54%): The purity was determined by RPLC (98%).

Sources & evidence

ORD record
ord-102665ef5b534d84b83a8646971078af
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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