Piperidine → 4-{(Glycylamino)methyl)-1-(4-fluorobenzyl)piperidine

HRID 1281003Notes

Reaction equation

HRID 1281003 reaction equation
C1C2C(COC([NH:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:26][CH2:25]3)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:18][CH2:19][C:20]([NH:22][CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:26][CH2:25]1)=[O:21]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 184261634-[{N-(9fluorenylmethyloxycarbonyl)glycyl}aminomethyl]-1(4-fluorobenzyl)piperidine

Product 1

HCID 184262334-{(Glycylamino)methyl)-1-(4-fluorobenzyl)piperidineYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the 4-[{N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]-1-(4-fluorobenzyl)piperidine and piperidine (5 mL) in DMF (5 mL) was stirred at room temperature for 17 h. Concentration and column chromatography (SiO2, Et3N:CH3OH:CH2Cl2=0.5:2:8) afforded 4-{(glycylamino)methyl}-1-(4-fluorobenzyl)piperidine (453 mg, 46%).

Workup

  1. concentrationConcentration and column chromatography (SiO2, Et3N:CH3OH:CH2Cl2=0.5:2:8)

Sources & evidence

ORD record
ord-96f2e845f6e6442c981602f25edccfb8
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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