ChemicalBook CAS DataBase List 1-Phenyl-[1,4]diazepane

1-Phenyl-[1,4]diazepane synthesis

5synthesis methods

Product Name:1-Phenyl-[1,4]diazepane
CAS Number:61903-27-3
Molecular formula:C11H16N2
Molecular Weight:176.26

tert-butyl 4-phenyl-1,4-diazepane-1-carboxylate

868063-55-2
3 suppliers
inquiry

61903-27-3
33 suppliers
$90.00/50mg

Yield:61903-27-3 100%

Reaction Conditions:

Stage #1: 4-phenyl-1,4-diazepane-1-carboxylic acid tert-butyl esterwith hydrogenchloride;methanol in 1,4-dioxane at 20; for 1 h;
Stage #2: with sodium hydrogencarbonate in water;

Steps:

57.57b

(57b) 1-phenyl-1,4-diazepane; 4N hydrochloric acid-dioxane solution (75 mL) was added to methanol (20 mL) solution of tert-butyl 4-phenyl-1,4-diazepane-1-carboxylate (16.58 g, 60.0 mmol) which was produced in Example 57 (57a) and the mixture was stirred at room temperature for one hour. The reaction liquid was concentrated, and a sodium hydrogen carbonate aqueous solution (100 mL) was added to the obtained residual substance, and extracted with a mixed solvent (3x100 mL) of methylene chloride/2-methylene chloride propanol (4:1) and after the extracted solvent was dried over sodium sulfate, the solvent was evaporated under reduced pressure and the title compound (10.57 g, yield 100%) was obtained. Yellow liquid IR (film) ν_max 2931, 1598, 1506, 1394, 1245, 1035, 748, 692 cm^-1; ¹H NMR(CDCl₃, 500 MHz) δ 1.87-1.92 (2H, m), 2.83 (2H, t, J = 5.9 Hz), 3.03 (2H, t, J = 5.9 Hz), 3.54-3.59 (4H, m), 6.65 (1H, t, J = 8.3 Hz), 6.70 (2H, d, J = 8.3 Hz), 7.21 (2H, t, J = 8.3 Hz); HRMS m/z calcd for C₁₁H₁₆N₂ 176.1313, found 176.1318; MS (EI) m/z: 176 [M⁺], 146, 134, 120, 106, 94, 77, 69, 43.

References:

EP1764367,2007,A1 Location in patent:Page/Page column 94

505-66-8 Synthesis