Acetonitrile → 4-[4-(3-Dimethylamino-propoxy)-phenyl)-3-oxo-butyronitrile

HRID 892084Notes

Reaction equation

HRID 892084 reaction equation
[C:1](#[N:3])[CH3:2].C([Li])CCC.C(O[C:12](=[O:27])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:16][CH:15]=1)C>C1COCC1.C1CCCCC1>[CH3:26][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C:12](=[O:27])[CH2:2][C:1]#[N:3])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6342Acetonitrile2×HCID 69220229HCID 69220229, compoundHCID 178418339Butyllithium

Product 1

HCID 222416434-[4-(3-Dimethylamino-propoxy)-phenyl)-3-oxo-butyronitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-78 °C

Procedure

The [4-(3-Dimethylamino-propxy)-phenyl]-acetic acid ethyl ester is then condensed with the lithium anion of acetonitrile by the following method: A solution of dry acetonitrile (0.627 mL) in 20 mL of THF, that had been cooled in a dry ice-acetone bath for 2 h under Ar(g), is treated dropwise with 6 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 2.45 gms. of [4-(3-dimethylamino-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 is then vacuum filtered affording the desired nitrile, 4-[4-(3-dimethylamino-propoxy)-phenyl]-3-oxo-butyronitrile, as a white solid (20–28% yield).

Workup

  1. additionis subsequently treated with 2.45 gms
  2. stirringto stir at −78° C. for an additional 30 minutes
  3. temperatureto warm to room temperature overnight
  4. filtrationvacuum filtered

Sources & evidence

ORD record
ord-f68b04b34caf481585a1bc7b8681e6ca
Source dataset
uspto-grants-2006_02
Patent number
US07005444B2

Reaction notes

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