Methyl iodide → HCID 69663221, compound

HRID 2212086Notes

Reaction equation

HRID 2212086 reaction equation
[CH2:1]([Li])CCC.[C:6]1([S:12]([CH2:15][C:16]([CH3:30])([CH3:29])[CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]([F:28])([F:27])[F:26])[CH2:21][CH2:20]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CI>O1CCCC1>[C:6]1([S:12]([CH:15]([CH3:1])[C:16]([CH3:30])([CH3:29])[CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH:22]([C:25]([F:28])([F:27])[F:26])[CH2:23][CH2:24]2)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 69663224HCID 69663224, compoundHCID 178418339Butyllithium

Product 1

HCID 69663221HCID 69663221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (1.5M, 0.13 ml, 0.2 mmol) in hexanes was added to a stirred solution of 1-(4-benzenesulfonyl-3,3-dimethyl-butyl)-4-trifluoromethylpiperidine (40 mg, 0.11 mmol) in tetrahydrofuran (2 ml) at −78° C. The mixture was stirred for 30 min. and methyl iodide (0.34 ml) was added. After 1 hour, the reaction mixture was quenched with one drop of water and concentrated in vacuo. The residue was purified on silica gel (dichloromethane:methanol) to give 1-(4-benzenesulfonyl-3,3-dimethyl-pentyl)-4-trifluoromethyl-piperidine. The title product was prepared by treatment of the amine with 1M ethereal HCl.

Workup

  1. waitAfter 1 hour
  2. customthe reaction mixture was quenched with one drop of water
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on silica gel (dichloromethane:methanol)

Sources & evidence

ORD record
ord-ed4b764ad15c48a0ac2592b9ae6aef42
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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