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

HRID 133607Notes

Reaction equation

HRID 133607 reaction equation
O1CCOCC1.Cl.[NH2:8][C:9]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1)=[O:16])=[O:12]>CO>[NH2:8][C:9]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1)=[O:16])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 184261834-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine

Product 1

HCID 184262164-[{N-(2-amino5-chlorobenzoyl)glycyl}aminomethyl]piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 M dioxane solution of HCl (9.5 mL) was added to a methanol (20 mL) solution of 4-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine (1.63 g, 3.84 mmol), and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated, and a 2 M aqueous solution of NaOH (20 mL) was added to the resulting residue. The obtained mixture was extracted with dichloromethane (20 mLX 3). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to thereby afford 4-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]piperidine (1.19 g, 95%). 1H NMR (CDCl3, 270 MHz) δ 1.10-1.76 (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 (M++H, C15H23ClN4O2).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiona 2 M aqueous solution of NaOH (20 mL) was added to the resulting residue
  3. extractionThe obtained mixture was extracted with dichloromethane (20 mLX 3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to thereby afford 4-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]piperidine (1.19 g, 95%)

Sources & evidence

ORD record
ord-f13d0f820398469a990b9926c31b1b37
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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