Amphetamine → HCID 53919021, compound

HRID 1494500Notes

Reaction equation

HRID 1494500 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 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. 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-1d40481a901b4babaab56748df170595
Source dataset
uspto-grants-1991_06
Patent number
US05026827

Reaction notes

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