Dextroamphetamine → (S)-N-(4-bromobenzylidene)-1-phenylpropan-2-amine

HRID 445322

Reaction equation

HRID 445322 reaction equation
[C:1]1([CH2:7][C@@H:8]([NH2:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[O-]S([O-])(=O)=O.[Mg+2]>C1C=CC=CC=1>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[N:10][C@@H:8]([CH3:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 5826DextroamphetamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 707414-Bromobenzaldehyde

Product 1

HCID 59536355(S)-N-(4-bromobenzylidene)-1-phenylpropan-2-amine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (S)-1-phenylpropan-2-amine (323 mg, 2389 μmol) in benzene (5 mL) was added 4-bromobenzaldehyde (442 mg, 2389 μmol and MgSO4 (500 mg, 4154 μmol) and the suspension was stirred at RT 4 h. The suspension was filtered and the solid washed with benzene (2×2 mL). The combined filtrates were concentrated to give (S)—N-(4-bromobenzylidene)-1-phenylpropan-2-amine which was used without purification in the next step.

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid washed with benzene (2×2 mL)
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-d15eecb1dc5347d78dc087d28ae62440
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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