Hydrochloric Acid → 4-[{N-(2-amino5-chlorobenzoyl)glycyl}aminomethyl]piperidine

HRID 279320Notes

Reaction equation

HRID 279320 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:9])=[O:5].Cl>CO.O1CCOCC1>[NH2:1][C:2]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)=[O:9])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 184261834-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine

Product 1

HCID 184262164-[{N-(2-amino5-chlorobenzoyl)glycyl}aminomethyl]piperidineYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[{(N-(2-amino-5-chlorobenzoyl)glycyl)amino}methyl]-1-(tert-butoxycarbonyl)piperidine (1.63 g, 3.84 mmol) in methanol (20 mL) was added 4 N HCl in dioxane (9.5 mL). The solution was stirred at room temperature for 6 h. The reaction mixture was concentrated and 2 N aqueous NaOH solution (20 mL) was added. The mixture was extracted with dichloromethane (20 mL×3), and the combined extracts were dried over sodium sulfate, filtered and concentrated to give 4-[{(N-(2-amino-5-chlorobenzoyl)glycyl)amino}methyl]piperidine (1.19 g, 95%): 1H NMR (CDCl3, 270 MHz) δ1.10-1.76 (m, 4H), 2.55 (td, J=2.4 and 12.2 Hz, 2H), 3.00-3.10 (m, 2H), 3.17 (t, J=6.2 Hz, 2H), 3.48 (s, 2H), 4.03 (d, J=4.9 Hz, 2H), 5.50 (br. s, 2H), 6.11-6.23 (m, 1H), 6.60 (d, J=8.8 Hz, 1H), 6.85-7.02 (m, 1H), 7.15 (dd, J=2.7 and 8.8 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H); ESI/MS m/e 325.2 (C15H21ClN4O2).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition2 N aqueous NaOH solution (20 mL) was added
  3. extractionThe mixture was extracted with dichloromethane (20 mL×3)
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-56f72b04946247ad8d19b5df706c99ca
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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