Water → 1-(Pyridin-2-yl)cyclopropanamine

HRID 1099081Notes

Reaction equation

HRID 1099081 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[N:8].[CH2:9]([Mg]Br)[CH3:10].O>CCOCC.O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([NH2:8])[CH2:10][CH2:9]1

Participants

7

Reactant 3

HCID 962WaterHCID 7522Pyridine-2-carbonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 111054091-(Pyridin-2-yl)cyclopropanamine

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-pyridinecarbonitrile (1.00 g, 9.60 mmol) in ether (30 mL) were added successively at RT titanium tetraisopropoxide (3.1 mL, 10.0 mmol) and 1.0 M of ethylmagnesium bromide in tetrahydrofuran (19 mL). After the mixture was stirred for 30 min, water (5.0 mL) was added. The mixture was extracted with diethyl ether. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to afford the crude product which was directly used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40241565bbbc4a889ebefa45ce0eb76e
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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