Diethyl Ether → HCID 22220766, compound

HRID 1794044Notes

Reaction equation

HRID 1794044 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].[Br:10][CH2:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].CCOCC>C(#N)C.CO>[Br-:10].[N:14]1([C:12](=[O:13])[CH2:11][N+:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[CH2:7][C:8]#[N:9])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 75959Pyridine-2-acetonitrileHCID 111061881-(Bromoacetyl)pyrrolidine2×

Product 1

HCID 22220766HCID 22220766, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

2-Pyridineacetonitrile (0.8 g, 6.77 mmole) and 1-(bromoacetyl)pyrrolidine (1.3 g, 6.77 mmole) were warmed to melt the 1-(bromoacetyl)pyrrolidine, then stirred at room temp. for 3 days. The mixture was dissolved in acetonitrile (5 mL) and ether (2 mL) and stored at 4 C for 3 days. The crystals which separated were filtered out to yield a crude product which was dissolved in methanol, decolorized, evaporated, and the residue triturated with 30% ether-acetonitrile to obtain 0.72 g of the title compound, mp 150–152 C.

Workup

  1. customThe crystals which separated
  2. filtrationwere filtered out
  3. customto yield a crude product which
  4. customevaporated
  5. customthe residue triturated with 30% ether-acetonitrile

Sources & evidence

ORD record
ord-c819da3836d245d7aa380e18cc27a69b
Source dataset
uspto-grants-2006_04
Patent number
US07022721B1

Reaction notes

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