Acetonitrile → HCID 22241718, compound

HRID 411735Notes

Reaction equation

HRID 411735 reaction equation
C(O[C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:8][CH:7]=1)C.[C:23](#[N:25])[CH3:24].C([Li])CCC>C1COCC1.C1CCCCC1>[N:16]1([CH2:15][CH2:14][CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:22])[CH2:24][C:23]#[N:25])=[CH:11][CH:10]=2)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 6342Acetonitrile2×HCID 69219508HCID 69219508, compound2×HCID 178418339Butyllithium

Product 1

HCID 22241718HCID 22241718, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-78 °C

Procedure

The [4-(3-morpholin-4-yl-propoxy)-phenyl]-acetic acid ethyl ester is then condensed with the lithium anion of acetonitrile by the following method: A solution of dry acetonitrile (0.254 mL) in 5 mL of THF, that had been cooled in a dry ice-acetone bath for 2 h under Ar(g), is treated dropwise with 2.43 mL of a 2M solution of n-butyl lithium in cyclohexane. This mixture is allowed to stir at −78° C. for an additional 1.5 h, and is subsequently treated with 1.15 gms. of [4-(3-morpholin-4-yl-propoxy)-phenyl]-acetic acid ethyl ester in dropwise fashion. The resulting solution is allowed to stir at −78° C. for an additional 30 minutes, and is then allowed to warm to room temperature overnight. The reaction mixture, subsequently, is vacuum filtered affording the desired nitrile, 4-[4-(3-morpholin-4-yl-propoxy)-phenyl]-3-oxo-butyronitrile, as a white solid (11% yield).

Workup

  1. additionis subsequently treated with 1.15 gms
  2. stirringto stir at −78° C. for an additional 30 minutes
  3. temperatureto warm to room temperature overnight
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ba05b4456eb64feeaed79dcceac8b025
Source dataset
uspto-grants-2003_05
Patent number
US06559173B1

Reaction notes

Loading…