Diphenylacetaldehyde → 1-(4-chlorobenzyl)-4-{N-(2,2-diphenylethyl)aminomethyl}piperidine

HRID 279295Notes

Reaction equation

HRID 279295 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.[C:17]1([CH:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-]>CO>[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][CH2:24][CH:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:4][CH2:5]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 13696DiphenylacetaldehydeHCID 28123BorohydrideHCID 18426145{[1-(4-Chlorobenzyl)piperidin-4-yl]methyl}amine

Product 1

HCID 184261581-(4-chlorobenzyl)-4-{N-(2,2-diphenylethyl)aminomethyl}piperidineYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reductive amination of 4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (120 mg) with 2,2-diphenylacetaldehyde (0.66 equiv.) and polymer-supported borohydride in methanol at 25° C. for 16 h, followed by general workup and column chromatography (SiO2) afforded 1-(4-chlorobenzyl)-4-{N-(2,2-diphenylethyl)aminomethyl}piperidine (70 mg, 49%): The purity was determined by RPLC (98%).

Sources & evidence

ORD record
ord-b18ae9a526c54caea7d2815eff3bbe4e
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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