ChemicalBook CAS DataBase List (Z)-3-(3-chloropropyl)-7,8-diethyl-1H-benzo[d] azepin-2 (3H)-one

(Z)-3-(3-chloropropyl)-7,8-diethyl-1H-benzo[d] azepin-2 (3H)-one synthesis

7synthesis methods

Product Name:(Z)-3-(3-chloropropyl)-7,8-diethyl-1H-benzo[d] azepin-2 (3H)-one
CAS Number:85175-59-3
Molecular formula:C15H18ClNO3
Molecular Weight:295.76

73942-87-7 Synthesis

7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

73942-87-7
306 suppliers
$23.00/1g

109-70-6 Synthesis

109-70-6
472 suppliers
$10.00/5g

(Z)-3-(3-chloropropyl)-7,8-diethyl-1H-benzo[d] azepin-2 (3H)-one

85175-59-3
238 suppliers
$6.00/250mg

Yield:85175-59-3 89%

Reaction Conditions:

Stage #1: 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-onewith potassium tert-butylate in dimethyl sulfoxide at 25 - 30; for 0.5 h;
Stage #2: 1.3-chlorobromopropane in dimethyl sulfoxide at 15 - 20; for 0.5 h;Reagent/catalyst;Time;Temperature;Concentration;

Steps:

1 EXAMPLE 1 Preparation of 7,8-dimethoxy-3- [3-chloropropyl]-1 ,3-dihydro-2H-3-benzazepin-2-one

A mixture of 7,8 -dimethoxy- 1,3 -dihydro-2H-3 -benzazepin-2-one (5 Og) and dimethylsulfoxide (350mL) was stirred for about 10mm and potassium tert-butoxide (30.7g) wasadded to it. The reaction mixture was stirred for about 30mm at about room temperature. A solution of 1-bromo-3-chloropropane (43.lg) in dimethyl sulfoxide (1 lOmL) was added to the stirred reaction mixture. The reaction mixture was cooled to about 15°C to about 20°C and stirred for about 30mm at about the same temperature. The reactionmixture was quenched into ice water and was stirred for about 3h. The solid obtained was filtered, washed with. water and dried under vacuum.Yield: 60g. (89%); HPLC purity:> 95%

References:

WO2014/102827,2014,A1 Location in patent:Paragraph 0120