1-(4-Chlorobenzyl)-4-[[(N-Boc-valyl)amino]methyl]piperidine → 1-(4-Chlorobenzyl)-4-[(valylamino)methyl]piperidine

HRID 133589Notes

Reaction equation

HRID 133589 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:28])[C@H:16]([CH:25]([CH3:27])[CH3:26])[NH:17]C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1>Cl.CO>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:15](=[O:28])[C@H:16]([CH:25]([CH3:27])[CH3:26])[NH2:17])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 187118021-(4-Chlorobenzyl)-4-[[(N-Boc-valyl)amino]methyl]piperidine

Product 1

HCID 537827311-(4-Chlorobenzyl)-4-[(valylamino)methyl]piperidineYield 97%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Conditions

Temperature
25 °C

Procedure

1-(4-Chlorobenzyl)-4-[[(N-Boc-valyl)amino]methyl]piperidine (1.1 g, 2.51 mmol) was dissolved in a 3 M HCl-methanol solution (25 mL) and stirred at 25° C. for 1 hour. The resulting reaction mixture was concentrated, and the obtained salt was dissolved in tBuOH/H2O=3:1 (25 mL). An anion (OH−) exchange resin was added until the solution became slightly basic. The obtained mixture was filtered and concentrated to provide 1-(4-chlorobenzyl)-4-[(valylamino)methyl]piperidine (819 mg, 97%). Further purification was not required for the resulting compound. ESI/MS m/e 338.1 (M++H, C18H28ClN3O).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe obtained salt was dissolved in tBuOH/H2O=3:1 (25 mL)
  4. additionAn anion (OH−) exchange resin was added until the solution
  5. filtrationThe obtained mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65c0d8cbe6fd471eba161484b6414d78
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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