Sodium Chloride → HCID 535945, compound

HRID 1358689Notes

Reaction equation

HRID 1358689 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=O)[CH2:2]2.[OH-].[K+].CCOP(OCC)([CH2:17][C:18]#[N:19])=O.[Na+].[Cl-]>O>[C:18]([CH:17]=[C:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)#[N:19]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium Hydroxide2×HCID 195073-QuinuclidinoneHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 535945HCID 535945, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a stirred solution of 3-quinuclidinone (50 g; 0.309 mol) in water (250 ml) was added potassium hydroxide (17.35 g; 0.309 mol). After 15 minutes, diethyl cyanomethyl phosphonate (109.6 g; 0.619 mol) was added with a further 125 ml water. A solution of potassium hydroxide (52.07 g; 0.928 mol) in water (250 ml) was added dropwise over 30 minutes. The reaction was left overnight, saturated with NaCl then extracted into ethyl acetate (6×200 ml). The organic extracts were combined, dried over anhydrous K2CO3 and concentrated in vacuo to give 3-cyanomethylidene quinuclidine (44 g; 96%, (96% pure-gc)) as a 2:1 mixture of Z:E isomers.

Workup

  1. extractionthen extracted into ethyl acetate (6×200 ml)
  2. dry with materialdried over anhydrous K2CO3
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-936de1e0c5f0477b9d3a1936375dbf11
Source dataset
uspto-grants-2003_07
Patent number
US06596869B2

Reaction notes

Loading…