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

HRID 1187091Notes

Reaction equation

HRID 1187091 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 h. 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. LC/MS: (IE, m/z) 307.09 [(M+1)−t-Bu]+.

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 h
  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-319fb52da71b49648513c295db976205
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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