Methyl iodide → HCID 178480351, compound
Reaction equation
[H-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:22][CH2:21]3)[CH2:14][CH2:13]2)=[CH:4]1.[CH3:32]I>O1CCCC1>[CH3:32][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:22][CH2:21]3)[CH2:14][CH2:13]2)=[CH:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of potassium hydride (0.24 g, 6 mmol) in tetrahydrofuran is cooled to 0° C. and a solution of trans 1-(2-{4-[1H-3-indolyl]cyclohexyl}ethyl)-4-(2-pyridinyl)piperazine (Example 1) (2.0 g, 5.14 mmol) in 20 mL of tetrahydrofuran is added. After 20 minutes 3 mL of methyl iodide is added and the reaction is warmed to room temperature overnight. The reaction is quenched with ammonium chloride and the tetrahydrofuran is removed under reduced pressure. The residue is partitioned between chloroform and ammonium chloride and the organics are dried with sodium sulfate and solvents are evaporated. The residue is chromatographed on silica gel (2% methanol in chloroform) to give the desired product.
Workup
- temperaturethe reaction is warmed to room temperature overnight
- customThe reaction is quenched with ammonium chloride
- customthe tetrahydrofuran is removed under reduced pressure
- customThe residue is partitioned between chloroform and ammonium chloride
- dry with materialthe organics are dried with sodium sulfate and solvents
- customare evaporated
- customThe residue is chromatographed on silica gel (2% methanol in chloroform)
Sources & evidence
- ORD record
- ord-8f868338526b460bae68a46125341e67
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05124332
Reaction notes
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