Sodium Cyanide → HCID 21934515, compound

HRID 1241438Notes

Reaction equation

HRID 1241438 reaction equation
Cl[CH2:2][CH2:3][C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1.[C-:14]#[N:15].[Na+]>CN(C=O)C.O>[N:13]1[C:12]2[NH:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:3][CH2:2][C:14]#[N:15]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 21934560HCID 21934560, compound

Product 1

HCID 21934515HCID 21934515, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

7-(2-chloroethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (500 mg) and NaCN (150 mg) were dissolved in DMF (in 15 mL) and the mixture was heated at 85° C. for 6 hrs. Cooled to 25° C. and the reaction was diluted with H2O, extracted with CHCl3, and the solution was washed with H2O, dried with MgSO4. The solution was concentrated to a yellow oil. Column purification (Ethyl acetate: Hexane=1:1) to yield a yellow solid 100 mg (8.9%). 1H NMR (DMSO-d6) δ 7.06 (d, 1H), 6.45 (m, 2H), 3.33 (1, 2H), 2.75 (m, 4H), 2.63 (t, 2H), 1.75 (m, 2H).

Workup

  1. temperatureCooled to 25° C.
  2. extractionextracted with CHCl3
  3. washthe solution was washed with H2O
  4. dry with materialdried with MgSO4
  5. concentrationThe solution was concentrated to a yellow oil
  6. customColumn purification (Ethyl acetate: Hexane=1:1)

Sources & evidence

ORD record
ord-1145d55f681e4c54aac6acf792708140
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

Loading…