Toluene → alpha-[2-[Bis(1-methylethyl)amino]ethyl]-alpha-(2-chlorophenyl)-2-pyridinepropanenitrile

HRID 1285530Notes

Reaction equation

HRID 1285530 reaction equation
[CH3:1][CH:2]([N:4]([CH:17]([CH3:19])[CH3:18])[CH2:5][CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])[C:8]#[N:9])[CH3:3].C[N:21](C)C=O.[C:25]1(C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH3:18][CH:17]([N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][N:21]=1)[C:8]#[N:9])[CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6228DimethylformamideHCID 126122112-(2-Chlorophenyl)-4-(diisopropylamino)butanenitrile

Product 1

HCID 14569342alpha-[2-[Bis(1-methylethyl)amino]ethyl]-alpha-(2-chlorophenyl)-2-pyridinepropanenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared by the method of Example 1 using 33 g (118 mmole) of α-[2-[bis(1-methylethyl)amino]ethyl]-2-chlorophenylacetonitrile instead of α-[2-[bis(1-methylethyl)amino]ethyl]phenylacetonitrile and dimethylformamide at 45°-50° instead of toluene at 65°-70°. After water was added to quench the reaction, the aqueous dimethylformamide solution was extracted with diethyl ether. The organic phase was separated, washed with water, and extracted into dilute aqueous hydrochloric acid. As in Example 1, the aqueous layer was made basic and extracted into dichloromethane, which was then dried and concentrated. The resultant oil was used in subsequent reactions without chromatographic purification. nmr (CDCl3): δ(ppm) 3.7 (pair of pseudo-d's, pyridyl-CH2 (isomers, each with non-equivalent H's)); 6.9-7.7 (m's, aromatic CH's); 8.35-8.55 (m, pyridine 6-H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe aqueous dimethylformamide solution was extracted with diethyl ether
  4. customThe organic phase was separated
  5. washwashed with water
  6. extractionextracted into dilute aqueous hydrochloric acid
  7. extractionextracted into dichloromethane, which
  8. customwas then dried
  9. concentrationconcentrated
  10. customThe resultant oil was used in subsequent reactions without chromatographic purification

Sources & evidence

ORD record
ord-11eddd28080d42698f32be17c47ad70b
Source dataset
uspto-grants-1986_01
Patent number
US04567270

Reaction notes

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