2,6-Dimethylpiperazine → HCID 57797816, compound

HRID 1948865Notes

Reaction equation

HRID 1948865 reaction equation
Cl.C(O[C:5](=[NH:37])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:14]=[CH:15][C:16]3[CH2:22][N:21]=[C:20]([C:23]4[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=4[F:30])[C:19]4[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:18]=4[C:17]=3[N:36]=2)=[CH:8][CH:7]=1)C.[CH3:38][CH:39]1[CH2:44][NH:43][CH2:42][CH:41]([CH3:45])[NH:40]1>C(O)C>[Cl:35][C:32]1[CH:33]=[CH:34][C:18]2[C:17]3[N:36]=[C:13]([NH:12][C:9]4[CH:10]=[CH:11][C:6]([C:5]([N:43]5[CH2:42][CH:41]([CH3:45])[NH:40][CH:39]([CH3:38])[CH2:44]5)=[NH:37])=[CH:7][CH:8]=4)[N:14]=[CH:15][C:16]=3[CH2:22][N:21]=[C:20]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=3[F:30])[C:19]=2[CH:31]=1

Participants

4

Reactant 2

HCID 660562,6-DimethylpiperazineHCID 68841695HCID 68841695, compound

Product 1

HCID 57797816HCID 57797816, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the ethyl benzimidate (100 mg, 0.17 mmol), 2,6-dimethylpiperazine (200 mg, 8.8 mmol), and absolute ethanol (1 mL) was submitted to microwave irradiation (300 W) for 7.5 minutes at 120° C. The reaction solution was cooled to room temperature and slowly poured into a stirring saline solution (10 mL). The resulting precipitate was collected and purified by column chromatography (silica gel, 0.25% NH4OH/2% MeOH/97.75% CH2Cl2 to 2.5% NH4OH/20% MeOH/77.5% CH2Cl2) to yield I-251 as a pale yellow solid (30 mg, 30%).

Workup

  1. customwas submitted to microwave irradiation (300 W) for 7.5 minutes at 120° C
  2. customThe resulting precipitate was collected
  3. custompurified by column chromatography (silica gel, 0.25% NH4OH/2% MeOH/97.75% CH2Cl2 to 2.5% NH4OH/20% MeOH/77.5% CH2Cl2)

Sources & evidence

ORD record
ord-4371481ece794d97a2cc38f0bd97dab2
Source dataset
uspto-grants-2013_03
Patent number
US08399659B2

Reaction notes

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