Allylamine → N-[2-(2-Fluorophenyl)ethyl]prop-2-en-1-amine
Reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>C(#N)C>[CH2:1]([NH:4][CH2:22][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[F:14])[CH:2]=[CH2:3]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
0.89 ml of allylamine (11.9 mmol) and 0.311 ml of diisopropyl ethylamine (1.78 mM) were added to the reaction solution (1.2 mmol) containing 350 mg of toluen-4-sulfonate-2-(2-fluoro-phenyl)-ethyl ester (u) prepared by above Step 1 dissolved in acetonitrile solution with stirring for 6 hrs at 80° C. After the reaction mixture was neutralized with 10% NaOH solution, the mixture was extracted with chloroform, washed with saturated NaCl solution, dried over MgSO4, filtered, and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:9) as an eluant to give 141 mg of allyl-[2-(2-fluoro-phenyl)-ethyl]-amine (v) (yield: 66%).
Workup
- customprepared by above Step 1
- extractionthe mixture was extracted with chloroform
- washwashed with saturated NaCl solution
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resultant was purified by Silica gel column chromatography with a solvent mixture
- additionmixed with methanol and chloroform (1:9) as an eluant
Sources & evidence
- ORD record
- ord-30879a59929c4d9ba47e329bc1e078fc
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846963B2
Reaction notes
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