Triphenylphosphine → 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]1[C:29]2[CH2:28][CH2:27][CH2:26][CH:25]([CH2:30][CH2:31]O)[C:24]=2[CH:23]=[CH:22]1.C(Cl)(Cl)(Cl)[Cl:34].C(#N)C>>[Cl:34][CH2:31][CH2:30][CH:25]1[CH2:26][CH2:27][CH2:28][C:29]2[N:21]([CH3:20])[CH:22]=[CH:23][C:24]1=2Participants
Procedure
Triphenylphosphine (2.46 g, 9.38 mmol) is added to a solution of 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanol (1.68 g, 9.38 mmol) in CCl4/Acetonitrile 1:1 (20 mL) at room temperature and the mixture is maintained under stirring for 3 hours monitoring the reaction by TLC. The solution is concentrated to half the volume at reduced pressure, CH2Cl2 is added and washed with water. The organic phase is separated and evaporated to dryness. The crude is treated with diethyl ether and the precipitated is filtered. The diethyl ether is evaporated at reduced pressure, and the resulting crude is purified by column chromatography, giving 4-(2-chloroethyl)-1-methyl-4,5,6,7-tetrahydro-1H-indole (0.8 g, 4.05 mmol, 43%, oil). (ESI-MS m/z 198 (M+H)+.
Workup
- temperaturethe mixture is maintained
- customthe reaction by TLC
- concentrationThe solution is concentrated to half the volume at reduced pressure, CH2Cl2
- additionis added
- washwashed with water
- customThe organic phase is separated
- customevaporated to dryness
- additionThe crude is treated with diethyl ether
- filtrationthe precipitated is filtered
- customThe diethyl ether is evaporated at reduced pressure
- customthe resulting crude is purified by column chromatography
Sources & evidence
- ORD record
- ord-f354015d5b914b869b6f71e3104e19bd
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481567B2
Reaction notes
Loading…