Potassium Cyanide → [1-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidin-3-yl]-acetonitrile

HRID 30300Notes

Reaction equation

C1OCCOCCOCCOCCOCCOC1.[C-:19]#[N:20].[K+].[CH2:22]([N:29]1[CH2:33][CH:32]([C:34]2[S:35][CH:36]=[C:37]([Br:39])[CH:38]=2)[CH:31]([CH2:40]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CS(C)=O.O>[CH2:22]([N:29]1[CH2:33][CH:32]([C:34]2[S:35][CH:36]=[C:37]([Br:39])[CH:38]=2)[CH:31]([CH2:40][C:19]#[N:20])[CH2:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

18-Crown-6 (5.3 g, 0.020 mol) and potassium cyanide (1.3 g, 0.020 mol) were added, respectively, to a solution of the product from step c) (6.7 g, 0.013 mol) in 50 mL of DMSO. The reaction mixture was heated at 80° C. overnight, cooled to room temperature, diluted with water (150 mL) and extracted with ethylacetate (3×150 mL). The combined organic extracts were washed with brine (200 mL), dried with MgSO4, and evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using 1-100% ethylacetate-hexane gradient to give the subtitle compound (2.1 g, yield: 44%). MS calculated for C17H17BrN2S+H: 361, observed: 361 and 363.

Workup

temperaturecooled to room temperature
extractionextracted with ethylacetate (3×150 mL)
washThe combined organic extracts were washed with brine (200 mL)
dry with materialdried with MgSO4
customevaporated in vacuo
customto give the crude product that
customwas purified by column chromatography (SiO2)

Sources & evidence

ORD record: ord-a59f58803f8347efb972f5bdd9d994b1
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

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