Sodium hydride → HCID 51111672, compound

HRID 1015381Notes

Reaction equation

HRID 1015381 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21](F)[C:18]=1[C:19]#[N:20]>CN(C=O)C>[C:6]([O:5][C:3]([N:10]1[CH2:11][CH2:12][N:13]([C:21]2[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[C:18]=2[C:19]#[N:20])[CH2:14][CH2:15]1)=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 51111672HCID 51111672, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a round bottom flask, sodium hydride (60%) (2.40 g; 60 mmol) was suspended in DMF (25 mL) and cooled in an ice water bath under nitrogen. 1-Boc-piperazine (9.53 g; 50.6 mmol) was added in small portions to the reaction mixture at 0° C. over 30 minutes. The mixture was allowed to stir at room temperature for 3 hours and the recooled to 0° C. 2,6-Difluorobenzonitrile (8.57 g; 60 mmol) was added to the reaction mixture in DMF (10 mL) over 45 minutes. The mixture was stirred at room temperature for 16 hours. The reaction mixture was poured in ice water (250 mL) and stirred. The solid was collected by vacuum filtration and washed with water. And then dried under vacuum to yield the title compound (11.65 g; 75% yield).

Workup

  1. temperaturecooled in an ice water bath under nitrogen
  2. customrecooled to 0° C
  3. stirringThe mixture was stirred at room temperature for 16 hours
  4. stirringstirred
  5. filtrationThe solid was collected by vacuum filtration
  6. washwashed with water
  7. customAnd then dried under vacuum

Sources & evidence

ORD record
ord-263f134ed7c748a19aaf1457b2fa19b8
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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