Water → HCID 13923375, compound

HRID 1073245Notes

Reaction equation

HRID 1073245 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][CH2:7][N:8]([CH3:25])[CH2:9][CH2:10][CH2:11][CH:12]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)[C:13]#[N:14].[NH2-].[Na+].[CH:31](Br)([CH3:33])[CH3:32].O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][CH2:7][N:8]([CH3:25])[CH2:9][CH2:10][CH2:11][C:12]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)([CH:31]([CH3:33])[CH3:32])[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 24533Sodium amideHCID 22158469HCID 22158469, compound

Product 1

HCID 13923375HCID 13923375, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

38.3 g (0.1 mole) of 5-[(3-methoxyphenethyl)-methylamino]-2-(3,5-dimethoxyphenyl)-valeronitrile were dissolved in 200 ml of toluene, and the stirred solution was refluxed with 4.7 g (0.12 mole) of powdered sodium amide for 1 hour. Thereafter, a solution of 15.7 g (0.12 mole) of isopropylbromide in 30 ml of toluene was added dropwise in the course of 60 minutes, and refluxing was continued for a further 2 hours. The cooled reaction mixture was poured into water, the toluene phase was washed several times with water and the toluene was then distilled off. The residue was dissolved in 100 ml of isopropanol, and ethanolic hydrochloric acid was added. The hydrochloride was recrystallized from isopropanol. 46.9 g (92%) of a hydrochloride of melting point 141°-143° C. were isolated.

Workup

  1. temperaturerefluxing
  2. customThe cooled reaction mixture
  3. washthe toluene phase was washed several times with water
  4. distillationthe toluene was then distilled off
  5. dissolutionThe residue was dissolved in 100 ml of isopropanol
  6. additionethanolic hydrochloric acid was added
  7. customThe hydrochloride was recrystallized from isopropanol

Sources & evidence

ORD record
ord-334dc10c12b943769b738d5eda3df20c
Source dataset
uspto-grants-1990_11
Patent number
US04968717

Reaction notes

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