Water → N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamine

HRID 642962Notes

Reaction equation

HRID 642962 reaction equation
[H-].[Na+].[CH:3]1([N:9]([CH3:13])[CH2:10][CH2:11][OH:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:14]([Sn:18]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19]I)[CH2:15][CH2:16][CH3:17].O>O1CCCC1.C(OCC)(=O)C>[CH3:13][N:9]([CH2:10][CH2:11][O:12][CH2:19][Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2775822-(Cyclohexylmethylamino)ethanolHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 59259719N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamineYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of sodium hydride (50%, 241 mg, 5.0 mmol) and tetrahydrofuran (20 ml) was added 2-[cyclohexyl(methyl)amino]ethanol (791 mg, 5.0 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 60° C. for 30 minutes. After the reaction mixture was cooled at 0° C. (external temperature), to the reaction mixture was added dropwise a solution of tributyl-iodomethyl-tin (2.2 g, 5.0 mmol) in tetrahydrofuran (5 ml), and the reaction mixture was stirred at 60° C. for 1 hour. After the reaction mixture was cooled at room temperature (external temperature), water was added to stop the reaction. Ethyl acetate was added to the reaction mixture, and the organic layer was separated. After the organic layer was washed with water, an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (790.7 mg, 4.3 mmol, 85%).

Workup

  1. temperatureAfter the reaction mixture was cooled at 0° C. (external temperature)
  2. stirringthe reaction mixture was stirred at 60° C. for 1 hour
  3. additionwas added
  4. customthe reaction
  5. customthe organic layer was separated
  6. washAfter the organic layer was washed with water
  7. distillationan aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel)

Sources & evidence

ORD record
ord-210dbaacbcd64b4dbdd1bdd888419e6a
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Reaction notes

Loading…