Malononitrile → HCID 131735661, compound

HRID 531412Notes

Reaction equation

HRID 531412 reaction equation
[Si:1]([C:8]1[C:9]([CH:21]=O)=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:23](#[N:27])[CH2:24][C:25]#[N:26].N1CCCCC1>CCO>[CH3:19][N:18]([CH3:20])[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:21]=[C:24]([C:23]#[N:27])[C:25]#[N:26])[C:8]([Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:17]2

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 89907148HCID 89907148, compound

Product 1

HCID 131735661HCID 131735661, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

415.7 mg (1.2616 mmol) of the compound 14 was dissolved in 9 mL of EtOH, and then added with 83.4 mg (1.2616 mmol) of malononitrile and 1 mL (12.616 mmol) of piperidine, and stirred for 3 hours at room temperature. When the reaction was completed, EtOH was removed by vacuum-distillating, and then the mixture was separated and purified by a column chromatography (eluent: EtOAc/n-hexane(v/v)=¼) without an additional extraction process to obtain 333.4 mg (70%) of an orange solid compound 15. 1H NMR (CDCl3, 300 MHz, 293K): δ 8.70(s, 1H), 8.24(s, 1H), 7.70-7.67(d, 1H), 7.02-6.98(dd, 1H), 6.88(s, 1H), 6.60-6.59(d, 1H), 3.14(s, 6H), 1.05(s, 9H), 0.31(s, 6H). 13C NMR(CDCl3, 75 MHz, 293K): δ 154.13, 152.53, 151.30, 140.20, 131.43, 131.09, 121.46, 119.27, 115.40, 114.88, 114.30, 111.78, 103.41, 40.29, 25.79, 18.38, −4.23. HRMS: m/z calcd. for C22H27N3OSi 377.1923 found 377.1923.

Workup

  1. customEtOH was removed by vacuum-distillating
  2. customthe mixture was separated
  3. custompurified by a column chromatography (eluent: EtOAc/n-hexane(v/v)=¼) without an additional extraction process

Sources & evidence

ORD record
ord-2bbf3f8c7d7d443a9303fad4e95a553a
Source dataset
uspto-grants-2016_05
Patent number
US09353399B2

Reaction notes

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