Amphetamine → HCID 53919021, compound

HRID 2253856Notes

Reaction equation

HRID 2253856 reaction equation
[NH2:1][CH:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3].Br[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[C:17]1(=[O:26])[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:1][CH:2]([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:3])[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]12

Participants

5

Reactant 3

HCID 3007AmphetamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 516892Sodium Bicarbonate

Product 1

HCID 53919021HCID 53919021, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.00 g of amphetamine (AP), 4.17 g of N-bromobutylphthalimide (manufactured by Aldrich Chemical Company Inc.) and 3.14 g of sodium hydrogen-carbonate was refluxed in 10 ml of benzene for 16 hours. After the solvent was removed from the reaction solution, the residue was purified by preparative thin layer chromatography (TLC, manufactured by Merck and Co. Inc.) using silica gel as the carrier. As an elution solvent, a mixture of methanol and chloroform in a volume ratio of 5:95 which had been previously saturated with ammonia was used the Rf value of the product was 0.7. Extraction of the product on silica gel with methanol gave 1.59 g of N-(4-phthalimidylbutyl)amphetamine (PIBAP).

Workup

  1. customAfter the solvent was removed from the reaction solution
  2. customthe residue was purified by preparative thin layer chromatography (TLC, manufactured by Merck and Co. Inc.)
  3. additionAs an elution solvent, a mixture of methanol and chloroform in a volume ratio of 5:95 which
  4. extractionExtraction of the product on silica gel with methanol

Sources & evidence

ORD record
ord-d11342add4b340338239f6c5ad21f4e9
Source dataset
uspto-grants-1993_08
Patent number
US05233025

Reaction notes

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