tert-Butyl piperazine-1-carboxylate → HCID 59568648, compound

HRID 2281334Notes

Reaction equation

HRID 2281334 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:11][O:10]2)[N:6]=[CH:5][C:4]=1[C:12]#[N:13].[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CCO>[C:12]([C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([CH:9]([OH:10])[CH2:11][N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)=[N:6][CH:5]=1)#[N:13]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 55296760HCID 55296760, compound

Product 1

HCID 59568648HCID 59568648, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 20 mL Pyrex vessel was charged with magnetic stirring bar, (1.68 g, 9.54 mmol) of 4-methoxy-6-(oxiran-2-yl)pyridine-3-carbonitrile, (2.66 g, 14.3 mmol) of tert-butyl piperazine-1-carboxylate, and 10 mL of EtOH. Then it was introduced in the microwave reactor and irradiated at 150° C. for 1 hour. The mixture was cooled to room temperature and the solvent was evaporated and the resulting residue was purified by column chromatography (silica gel, 1-10% MeOH/dichloromethane) which afforded the product as an isomeric mixtures.

Workup

  1. additionA 20 mL Pyrex vessel was charged with magnetic stirring bar
  2. additionThen it was introduced in the microwave reactor
  3. customirradiated at 150° C. for 1 hour
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by column chromatography (silica gel, 1-10% MeOH/dichloromethane) which
  6. customafforded the product as an isomeric mixtures

Sources & evidence

ORD record
ord-f41168b159554822950f264630323228
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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