Toluene → HCID 12612263, compound

HRID 2163436Notes

Reaction equation

HRID 2163436 reaction equation
[CH:1]([N:4]([CH:16]([CH3:18])[CH3:17])[CH2:5][CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9])([CH3:3])[CH3:2].[NH2-].[Na+].C1(C)C=CC=CC=1.Cl[CH2:29][CH2:30][N:31]1[CH2:37][CH:36]2[CH2:38][CH2:39][CH:33]([CH2:34][CH2:35]2)[CH2:32]1>O>[CH:16]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][C:7]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH2:29][CH2:30][N:31]1[CH2:37][CH:36]2[CH2:38][CH2:39][CH:33]([CH2:34][CH2:35]2)[CH2:32]1)[C:8]#[N:9])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 161463-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonaneHCID 24533Sodium amideHCID 126122104-Diisopropylamino-2-phenyl-butyronitrile

Product 1

HCID 12612263HCID 12612263, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 16 parts of α-[2-(diisopropylamino)ethyl]-α-phenylacetonitrile and 5 parts of sodium amide in 200 parts by volume of toluene is heated to about 100° C. over a period of 15 minutes and then 20 parts of 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane in 100 parts by volume of toluene is added slowly over a period of 20 minutes. This mixture is heated at 105°-110° C. for an hour and then cooled to room temperature when 200 parts by volume of water is added. The organic layer is separated, dried over calcium sulfate, concentrated, and then distilled to afford 2-[2-(diisopropylamino)ethyl]-2-phenyl-4-(3-azabicyclo[3.2.2]non-3-yl)butyronitrile, as an oil. This compound is represented by the following structural formula ##STR16##

Workup

  1. temperatureThis mixture is heated at 105°-110° C. for an hour
  2. additionis added
  3. customThe organic layer is separated
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-1e84d29fbd134120be10a46306061ab2
Source dataset
uspto-grants-1979_01
Patent number
US04134890

Reaction notes

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