Potassium Carbonate → HCID 19744520, compound

HRID 2254399Notes

Reaction equation

HRID 2254399 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:17])[CH:16]=1)[CH2:12]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:18].[CH3:19][NH:20][CH2:21]/[CH:22]=[CH:23]/[C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:18].[CH3:27][C:26]([CH3:29])([CH3:28])[C:25]#[C:24]/[CH:23]=[CH:22]/[CH2:21][N:20]([CH2:12][C:11]1[CH:14]=[C:15]([CH3:17])[CH:16]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19744727HCID 19744727, compoundHCID 19917487(E)-N-methyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

Product 1

HCID 19744520HCID 19744520, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzyloxy-5-methylbenzyl bromide (118 mg) and 76 mg of (E)-N-methyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride were dissolved in 25 ml of dimethylformamide, and 67 mg of potassium carbonate was added. The mixture was stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure, and the residue was purified by preparative thin-layer chromatography [thin layer plate: Kieselgel 60F254, Art. 5715 (a product of E. Merck Co.); developing solvent: hexane/ethyl acetate=4/1]. The purified compound was then converted into a hydrochloride using HCl methanol solution. Treatment with a mixture of tetrahydrofuran and hexane gave 102 mg (yield 60.9%) of the captioned compound as a colorless crystalline powder having a melting point of 180° to 186° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue was purified by preparative thin-layer chromatography [thin layer plate
  3. additionTreatment with a mixture of tetrahydrofuran and hexane

Sources & evidence

ORD record
ord-642622f06ba34f7c99f2f4cfa02a24d4
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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