Isobutylene oxide → [1-(2-Hydroxy-2-methyl-propyl)-piperidin-4-yl]-carbamic acid ethyl ester

HRID 1928878Notes

Reaction equation

HRID 1928878 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11])[CH2:3][CH2:2]1.[CH3:13][C:14]1([O:17][CH2:16]1)[CH3:15]>C(O)C>[CH2:10]([O:9][C:8](=[O:12])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])[CH2:6][CH2:5]1)[CH3:11]

Participants

4

Reactant 2

HCID 11208Isobutylene oxideHCID 15595030ethyl N-(piperidin-4-yl)carbamate

Product 1

HCID 68631449[1-(2-Hydroxy-2-methyl-propyl)-piperidin-4-yl]-carbamic acid ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of commercially available ethyl piperidin-4-ylcarbamate (2.067 g, 12 mmol) and isobutylene oxide (868 mg, 12 mmol) in ethanol (15 mL) was irradiated in a microwave apparatus at 110° C. for 90 min. Purification by silica gel column chromatography with ethyl acetate gave the title compound as a colorless oil (2.838 g, 97%); MS: m/e=245.3 (M+H+).

Workup

  1. customwas irradiated in a microwave apparatus at 110° C. for 90 min
  2. customPurification by silica gel column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-7bc56b8899dd4890b9e22e4953127a5f
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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