Hydrochloric Acid → HCID 17823029, compound

HRID 133581Notes

Reaction equation

HRID 133581 reaction equation
O1CCOCC1.Cl.[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:32])[CH2:23][NH:24]C(OC(C)(C)C)=O)[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH2:8]([N:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:32])[CH2:23][NH2:24])[CH2:19][CH2:20]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 184261311,1-Dimethylethyl N-[2-oxo-2-[[1-(phenylmethyl)-4-piperidinyl]amino]ethyl]carbamate

Product 1

HCID 17823029HCID 17823029, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 M dioxane solution of HCl was added to a methanol (80 mL) solution of 1-benzyl-4-[N-(tert-butoxycarbonyl)glycyl]aminopiperidine (6.59 g). The resulting solution was stirred at room temperature for 2 hours and concentrated. A 2 M aqueous solution of NaOH (20 mL) was then added to the solution. The resulting mixture was extracted with dichloromethane (40 mL). The extracts were combined, dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate/methanol/triethylamine=85:12:3) to thereby provide 1-benzyl-4-(glycylamino)piperidine (3.91 g, 83%). 1H NMR (CDCl3, 400 MHz) δ 1.47-1.59 (m, 2H), 1.59 (br, 2H), 1.76-1.96 (m, 2H), 2.10-2.19 (m, 2H), 2.75-2.87 (m, 2H), 3.29 (s, 2H), 3.50 (s, 2H), 3.65-3.89 (m, 1H), 7.15-7.23 (m, 1H), 7.23-7.33 (m, 5H).

Workup

  1. concentrationconcentrated
  2. additionA 2 M aqueous solution of NaOH (20 mL) was then added to the solution
  3. extractionThe resulting mixture was extracted with dichloromethane (40 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by column chromatography (SiO2, ethyl acetate/methanol/triethylamine=85:12:3) to thereby provide 1-benzyl-4-(glycylamino)piperidine (3.91 g, 83%)

Sources & evidence

ORD record
ord-8805416ac2484be6bfb03ceeeb7d5eb3
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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