Dimethylamine → 2-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one hydrochloride

HRID 4826

Reaction equation

[CH3:1][NH:2][CH3:3].[Cl:4][CH2:5][CH2:6][CH:7]1[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[C:10]2[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=2[O:8]1>C(O)C>[ClH:4].[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][CH:7]1[CH2:13][N:12]([CH3:14])[C:11](=[O:15])[C:10]2[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=2[O:8]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 9 g (0.2 mole) of dimethylamine in 250 ml of ethanol was added to 24 g (0.1 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one in a steel bomb. The mixture was heated at 100° C. for 18 hrs. The solution was concentrated in vacuo and the residue partitioned between ethyl acetate and dilute sodium hydroxide. The ethyl acetate layer was concentrated and the residue comprised substantially of the free base of the title compound was dissolved in methyl isobutyl ketone-isopropanol mixture. The solution was acidified with hydrogen chloride gas to give the title compound, m.p. 188°-197° C.

Workup

concentrationThe solution was concentrated in vacuo
customthe residue partitioned between ethyl acetate and dilute sodium hydroxide
concentrationThe ethyl acetate layer was concentrated
dissolutionthe residue comprised substantially of the free base of the title compound was dissolved in methyl isobutyl ketone-isopropanol mixture

Sources & evidence

ORD record: ord-66c07ea6a9ef4116951cdf9662a6bd01
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727152

Linked notes

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