2-Bromopropane → HCID 13923376, compound

HRID 1073246Notes

Reaction equation

HRID 1073246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[K+].[CH:14](Br)([CH3:16])[CH3:15].Cl[CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:23]>C1(C)C=CC=CC=1.C(N(CCOCCOC)CCOCCOC)COCCOC.O>[CH2:24]([N:22]([CH3:23])[CH2:21][CH2:20][CH2:19][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH:14]([CH3:16])[CH3:15])[C:10]#[N:11])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 13473134HCID 13473134, compound

Product 1

HCID 13923376HCID 13923376, compoundYield 71.6%

Reagents, catalysts & solvents 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-CatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

13.5 g (0.1 mole) of 3-methoxyphenylacetonitrile were dissolved in 15 ml of toluene, and 52 g (0.8 mole) of 85% strength potassium hydroxide powder and 0.2 g of tris(3,6-dioxaheptyl)-amine were added. Thereafter, 12.3 g (0.1 mole) of isopropyl bromide were added dropwise to the stirred mixture at a rate such that the reaction temperature did not exceed 50° C. When the addition was complete, stirring was continued for 2 hours at 50° C., after which a solution of 21.2 g (0.1 mole) of N-(3-chloropropyl)-N-methylphenethylamine in 20 ml of toluene was added at 90° C. The reaction mixture was stirred for a further 3 hours at 90° C. and cooled, after which 100 ml of water were added and the toluene phase was separated off. The toluene was distilled off to give a yellow oil, which was chromatographed over a silica gel column using a solvent mixture consisting of 9:1:0.5 methylene chloride/acetone/ methanol. The chromatographically pure base was dissolved in ethyl acetate, and the hydrochloride was precipitated with ethanolic hydrochloric acid. 26.1 g (65%) of a product of melting point 154°-156° C. were obtained.

Workup

  1. customdid not exceed 50° C
  2. additionWhen the addition
  3. stirringThe reaction mixture was stirred for a further 3 hours at 90° C.
  4. temperaturecooled
  5. customthe toluene phase was separated off
  6. distillationThe toluene was distilled off
  7. customto give a yellow oil, which
  8. customwas chromatographed over a silica gel column
  9. dissolutionThe chromatographically pure base was dissolved in ethyl acetate
  10. customthe hydrochloride was precipitated with ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-4b3b8c04807446898912c0c7991577db
Source dataset
uspto-grants-1990_11
Patent number
US04968717

Reaction notes

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