Methylamine → HCID 9817507, compound

HRID 1030470Notes

Reaction equation

HRID 1030470 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.[CH3:20][NH2:21]>C(O)C>[ClH:1].[CH3:20][N:21]1[CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19820413HCID 19820413, compound

Product 1

HCID 9817507HCID 9817507, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 6.2 g of 2-(2-chloroethoxy)-1-[2-(chloromethyl)phenoxy]benzene in 310 ml ethanol was added at room temperature in 45 min to a solution of 80 ml of methylamine in 1.2 1 of abs. ethanol. The mixture was stirred overnight, concentrated and dissolved in 100 ml of dimethyl sulphoxide. 18.6 ml of triethylamine were added and the reaction mixture was heated to 90°-100° C. and stirred overnight. After cooling the mixture was poured into 4.5 1 of ice water and extracted with 3×600 ml of dichloromethane. The extract was washed with water, dried over sodium sulphate and concentrated in vacuo. The crude product obtained was purified by silica chromatography with dichloromethane-acetone (9:1), after which the free base was converted into the hydrochloric salt, to obtain 2.12 g (35%) of 6,7,8,9-tetrahydro-8-methyl-dibenzo[b,i][1,4,7]dioxazecine hydrochloride. Mp 223° C.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in 100 ml of dimethyl sulphoxide
  3. addition18.6 ml of triethylamine were added
  4. temperaturethe reaction mixture was heated to 90°-100° C.
  5. stirringstirred overnight
  6. temperatureAfter cooling the mixture
  7. additionwas poured into 4.5 1 of ice water
  8. extractionextracted with 3×600 ml of dichloromethane
  9. washThe extract was washed with water
  10. dry with materialdried over sodium sulphate
  11. concentrationconcentrated in vacuo
  12. customThe crude product obtained
  13. customwas purified by silica chromatography with dichloromethane-acetone (9:1)

Sources & evidence

ORD record
ord-3a044bdb694d4a4b97d20c2335e15a29
Source dataset
uspto-grants-1992_04
Patent number
US05106839

Reaction notes

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