Piperidine → HCID 18426261, compound

HRID 279302Notes

Reaction equation

HRID 279302 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]([S:37][CH3:38])=[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]([S:37][CH3:38])=[CH:33][CH:32]=2)[CH2:26][CH2:25]1)=[O:21]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 18426207HCID 18426207, compound

Product 1

HCID 18426261HCID 18426261, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(N-(9-fluorenylmethyloxycarbonyl)glycyl}aminomethyl]-1-(4-methylthiobenzyl)piperidine (590 mg) and piperidine (1 mL) in DMF (4 mL) was stirred at room temperature for 2 h. Concentration and column chromatography (SiO2, Et3N:CH3OH:CH2Cl2=1:1:9) afforded 4-{(glycylamino)methyl}-1-(4-methylthiobenzyl)piperidine (365 mg) as a white solid: 1H NMR (CDCl3, 270 MHz) δ1.25 (dd, J=12 Hz, 4.1 Hz, 2H), 1.34 (dd, J=12 Hz, 4.1 Hz, 2H), 1.51 (br-s, 2H), 1.66 (d, J=12 Hz, 2H), 1.77 (d, J=7.3 Hz, 1H), 1.94 (t, J=9.5 Hz, 2H), 2.48 (s, 3H), 2.80 (d, J=12 Hz, 2H), 3.18 (t, J=6.2 Hz, 2H), 3.35 (s, 2H), 3.45 (s, 2H), 7.18-7.29 (m, 4H), 7.35 (br-s, 1H).

Workup

  1. concentrationConcentration and column chromatography (SiO2, Et3N:CH3OH:CH2Cl2=1:1:9)

Sources & evidence

ORD record
ord-059f27ca312b4cffa1dedec618ffebca
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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