Methyl iodide → HCID 18406201, compound

HRID 1016221Notes

Reaction equation

HRID 1016221 reaction equation
[CH3:1][I:2].[N:3]1([CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]2[C:24]([OH:25])=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[O:14])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1>ClC1C=CC=CC=1>[I-:2].[OH:25][C:24]1[C:15]([C:13]([NH:12][CH2:11][CH2:10][CH2:9][N+:3]2([CH3:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[O:14])=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 824142-Naphthalenecarboxamide, 3-hydroxy-N-[3-(4-morpholinyl)propyl]-

Product 1

HCID 18406201HCID 18406201, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

6.2 g of methyl iodide were added dropwise at 80° C. to a solution of 12.6 g of 3-hydroxynaphthalene-2-carboxylic acid (3-morpholin-4-ylpropyl)amide (RN 10155-47-2) in 60 ml of chlorobenzene. After refluxing for 4 hours, the suspension was cooled, filtered on a sinter funnel and spin-filtered. The white precipitate was washed with 20 ml of chlorobenzene and then with 20 ml of petroleum ether. The precipitate was then dried under vacuum. 12.5 g of a white solid of 4-{3-[(3-hydroxynaphthalene-2-carbonyl)amino]propyl}-4-methylmorpholin-4-ium iodide were obtained in a yield of 69%, melting at a temperature above 260° C. (Kofler) and the elemental analysis of which, calculated for C19H25N2O3.I, was:

Workup

  1. temperatureAfter refluxing for 4 hours
  2. temperaturethe suspension was cooled
  3. filtrationfiltered on a sinter funnel
  4. filtrationspin-filtered
  5. washThe white precipitate was washed with 20 ml of chlorobenzene
  6. customThe precipitate was then dried under vacuum

Sources & evidence

ORD record
ord-9e2d3f1a839a48a0b3e3078e814db577
Source dataset
uspto-grants-2002_11
Patent number
US06475247B1

Reaction notes

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