Methyl iodide → HCID 68151500, compound

HRID 1400281Notes

Reaction equation

HRID 1400281 reaction equation
[Cl-].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][NH2+:16][CH2:17][C:18]1[O:19][CH:20]=[CH:21][CH:22]=1.[C:23]([O-])([O-])=O.[K+].[K+].CI>C1COCC1>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][N:16]([CH2:17][C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)[CH3:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86709752HCID 86709752, compound

Product 1

HCID 68151500HCID 68151500, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (32 mg, 0.095 mmol) of 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2 ylmethyl)ethanaminium chloride (1) in 5 mL of THF was treated with 21 mg (0.15 mmol) of K2CO3 and 6 μL (0.100 mmol) of MeI. The resulting mixture was stirred for 14 h at room temperature. The solvent was distilled off under vacuum and the crude was triturated for 1 h in 5 mL of di-isopropyl ether. Pure 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)-N-methylethanamine was obtained after decantation of ether as a pale yellow oil in 91% yield.

Workup

  1. distillationThe solvent was distilled off under vacuum
  2. customthe crude was triturated for 1 h in 5 mL of di-isopropyl ether

Sources & evidence

ORD record
ord-7ac51e5c8839401ca9a1d04e17246c6c
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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