Water → HCID 68289215, compound

HRID 541331Notes

Reaction equation

HRID 541331 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:18]([CH2:29][CH3:30])=[CH:19][C:20]([CH2:27][CH3:28])=[C:21]([CH:26]=3)[C:22]([NH:24][NH2:25])=[O:23])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O.C(=O)(O)[O-].[Na+].Br[C:38]#[N:39]>O1CCOCC1>[NH2:39][C:38]1[O:23][C:22]([C:21]2[C:20]([CH2:27][CH3:28])=[CH:19][C:18]([CH2:29][CH3:30])=[C:17]([CH:26]=2)[C:15]([N:12]2[CH2:13][CH2:14][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[CH2:10][CH2:11]2)=[O:16])=[N:24][N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 68288786HCID 68288786, compound2×

Product 1

HCID 68289215HCID 68289215, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a round-bottom flask was added a solution of 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2,4-diethylbenzohydrazide (compound 204.7, 100 mg, 0.220 mmol, 1.00 equiv, 90%) in a solvent mixture of water (2 mL) and dioxane (3 mL). Sodium bicarbonate (62 mg, 0.740 mmol, 3.00 equiv) was added to the reaction mixture at room temperature, and stirred for 5 minutes. BrCN (75 mg, 0.740 mmol, 3.00 equiv) was then added to the reaction at room temperature. The resulting solution was stirred for 2 h at room temperature, then quenched with 30 mL of FeSO4 (aq., sat.) and diluted with ethyl acetate. The resulting mixture was stirred vigorously then filtered through celite and washed with 1 M FeSO4, water, and ethyl acetate. The layers were separated and the aqueous phase was extracted with 2×50 mL of ethyl acetate. The combined organic layers were washed with 2×50 mL of brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. This resulted in 100 mg (89%) of the title compound as a yellow solid. The compound was used in the next step reaction without further purification.

Workup

  1. stirringThe resulting solution was stirred for 2 h at room temperature
  2. customquenched with 30 mL of FeSO4 (aq., sat.)
  3. additiondiluted with ethyl acetate
  4. stirringThe resulting mixture was stirred vigorously
  5. filtrationthen filtered through celite
  6. washwashed with 1 M FeSO4, water, and ethyl acetate
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted with 2×50 mL of ethyl acetate
  9. washThe combined organic layers were washed with 2×50 mL of brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c57c88f21b541ff90d03576f139710e
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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