Triethylamine → 4-[{N-(9fluorenylmethyloxycarbonyl)glycyl}aminomethyl]-1(4-fluorobenzyl)piperidine

HRID 1281002Notes

Reaction equation

HRID 1281002 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1.CCN(CC)CC>CC#N>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([CH2:35][C:34]4[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=4)[CH2:26][CH2:25]3)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 680214-Fluorobenzyl bromideHCID 543594714-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine

Product 1

HCID 184261634-[{N-(9fluorenylmethyloxycarbonyl)glycyl}aminomethyl]-1(4-fluorobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]piperidine (1.50 g, 3.49 mmol), 4-fluorobenzyl bromide (0.478 mL, 3.84 mmol), and Et3N (1.47 mL, 10.5 mmol) in CH3CN (200 mL) was stirred at room temperature for 13 h and concentrated. Column chromatography (SiO2, 10% CH3OH/CH2Cl2) afforded 4-[{N-(9fluorenylmethyloxycarbonyl)glycyl}aminomethyl]-1(4-fluorobenzyl)piperidine

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ace41d60398f45439b8fa33f7ae11c8a
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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