Piperidine → HCID 18426261, compound

HRID 133593Notes

Reaction equation

HRID 133593 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, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A DMF (4 mL) solution of 4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]-1-(4-methylthiobenzyl)piperidine (590 mg) and piperidine (1 mL) was stirred at 60° C. for 2 hours. After concentrating, the obtained crude product was purified by column chromatography (SiO2,triethylamine/methanol/dichloromethane=1:1:9) to thereby afford 4-[(glycylamino)methyl]-1-(4-methylthiobenzyl)piperidine (365 mg) as a white solid. 1H NMR (CDCl3, 270 MHz) δ 1.25 (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. concentrationAfter concentrating
  2. customthe obtained crude product
  3. customwas purified by column chromatography (SiO2,triethylamine/methanol/dichloromethane=1:1:9) to thereby afford 4-[(glycylamino)methyl]-1-(4-methylthiobenzyl)piperidine (365 mg) as a white solid

Sources & evidence

ORD record
ord-aff5e927df754d1fa0bd4c35887a545f
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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