Potassium Cyanide → 1,4-Bis(tert-butoxycarbonyl)-2-(2-cyanoethyl)piperazine

HRID 352889Notes

Reaction equation

[C-:1]#[N:2].[K+].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[CH2:24][CH2:25]Br)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)C>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[CH2:24][CH2:25][C:1]#[N:2])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 110 °C

Procedure

To an aqueous solution (3.0 ml) of potassium cyanide (85.0 mg) was added a solution of 1,4-bis(t-butoxycarbonyl)-2-(2-bromoethyl)piperazine (393 mg) in ethanol (3.0 ml), followed by stirring under heat at 110° C. for 3 hours. After the removal of ethanol by distillation under reduced pressure, methylene chloride (100 ml) was added to the residue. The organic layer was washed with distilled water until the water phase became neutral. The resulting organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (silica gel 15 g, hexane:ethyl acetate=2:1), whereby the title compound (145.0 mg, 43%) was obtained as a white solid.

Workup

customAfter the removal of ethanol
distillationby distillation under reduced pressure, methylene chloride (100 ml)
additionwas added to the residue
washThe organic layer was washed with distilled water until the water phase
washThe resulting organic layer was washed with saturated aqueous NaCl solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customwas obtained as a white solid

Sources & evidence

ORD record: ord-0a66c9f0c40746e19510fbcf077bc6db
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747023B1

Reaction notes

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