Hydrochloric Acid → Benzyl (piperidin-3-ylmethyl)carbamate hydrochloride

HRID 896529Notes

Reaction equation

HRID 896529 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:9]1)=O)(C)(C)C.[ClH:26].O1CCOCC1>C(OCC)(=O)C>[ClH:26].[CH2:19]([O:18][C:16]([NH:15][CH2:14][CH:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 451587943-(Benzyloxycarbonylaminomethyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 22350243Benzyl (piperidin-3-ylmethyl)carbamate hydrochlorideYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(benzyloxycarbonylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester (594 mg, 1.7 mmol) in ethyl acetate (10 mL) was stirred on an ice bath and treated with a solution of hydrogen chloride in dioxane (4.0 N, 10 mL, 40 mmol). The mixture was stirred for 80 minutes, then was concentrated under vacuum. The gummy residue was triturated repeatedly in ether to provide a white powder (408 mg, 84%)which was extremely hygroscopic and was used without further purification. 1H NMR (300 MHz, CD3OD) δ7.34 (m, 5H), 5.07 (s, 2H), 3.34 (m, 2H), 3.09 (m, 2H), 2.88 (m, 1H), 2.66 (m, 1H), 1.90 (m, 3H), 1.70 (m, 1H), 1.30 (m, 1H).

Workup

  1. concentrationwas concentrated under vacuum
  2. customThe gummy residue was triturated repeatedly in ether

Sources & evidence

ORD record
ord-380bef6e02f34784aec9917def9ff058
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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