Hydrochloric Acid → HCID 18426167, compound

HRID 1280987Notes

Reaction equation

HRID 1280987 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:25])[CH2:16][NH:17]C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>CO.O1CCOCC1>[Cl:26][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:25])[CH2:16][NH2:17])[CH2:10][CH2:9]2)=[CH:3][CH:4]=1

Participants

5

Reactant 2

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

Product 1

HCID 18426167HCID 18426167, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-benzyl-4-{N-(tert-butoxycarbonyl)glycyl}aminopiperidine (6.59 g) in methanol (80 mL) was added 4 N HCl in dioxane (19 mL). The solution was stirred at room temperature for 2 h. The reaction mixture was concentrated and 2 N aqueous NaOH solution (20 mL) was added. The mixture was extracted with dichloromethane (40 mL×3), and the combined extracts were dried over anhydrous sodium sulfate and concentrated. Column chromatography (SiO2, AcOEt/MeOH/Et3N=85/12/3) gave 1-(4-chlorobenzyl)-4-(glycylamino)piperidine (3.91 g, 83%): 1H NMR (CDCl3, 400 MHz) d 1.47-1.59 (m, 2 H), 1.59 (br, 2 H), 1.76-1.96 (m, 2 H), 2.10-2.19 (m, 2 H), 2.75-2.87 (m, 2 H), 3.29 (s, 2 H), 3.50 (s, 2 H), 3.65-3.89 (m, 1 H), 7.15-7.23 (m, 1 H), 7.23-7.33 (mn, 5 H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition2 N aqueous NaOH solution (20 mL) was added
  3. extractionThe mixture was extracted with dichloromethane (40 mL×3)
  4. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af6a8d114274461c97fbe44317224b91
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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