ChemicalBook CAS DataBase List 5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE

5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE synthesis

5synthesis methods

Product Name:5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE
CAS Number:16036-79-6
Molecular formula:C17H18ClN
Molecular Weight:271.78

494-19-9 Synthesis

494-19-9
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$6.00/25g

109-70-6 Synthesis

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

5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE

16036-79-6
10 suppliers
$95.00/5mg

Yield:16036-79-6 40%

Reaction Conditions:

Stage #1: 9,10-dihydrodibenzazepinewith sodium amide in toluene at 25; for 0.5 h;
Stage #2: 1.3-chlorobromopropane in toluene at 115; for 14 h;

Steps:

12 1.1.3. 5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine.(10c).

A solution of azapine (1.0 g, 5.12 mmol) in dry toluene (15 mL) was added to the suspension of sodium amide (0.5 g, 12.80 mmol) in dry toluene 5 (mL). After stirring at room temprature (25 °C) for 30 minutes, 1-bromo-3-chloropropane (0.94 g, 1.23 ml, 10.14 mmol) was added drop-wise to the reaction mixture. The resulting reaction mixture was refluxed (115 °C) for another 14 hours.. After completion of reaction (TLC), cooled to 0 °C, quenced with brine and extracted with ethyl acetate (3 × 15 ml). The combined ethylacetate extracts were dried over sodium sulphate and concentrated in vacuo to obtain 10c as an oil (0.83 g, 40%). 1H-NMR (400 MHz, CDCl3) δ 7.22-7.10 (m, 6H), 6.99 (td, J = 7.6 and 1.2 Hz, 2H), 3.96 (t, J = 6.4 Hz, 2H), 3.62 (t, J = 6.4 Hz, 2H), 3.21 (s, 4H), 2.27 (quin, J = 6.4 Hz, 2H).

References:

Kumar, Malkeet;Singh, Kawaljit;Ngwane, Andile H.;Hamzabegovic, Fahreta;Abate, Getahun;Baker, Bienyameen;Wiid, Ian;Hoft, Daniel F.;Ruminski, Peter;Chibale, Kelly [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 4,p. 833 - 844] Location in patent:supporting information

494-19-9 Synthesis

494-19-9
329 suppliers
$6.00/25g

109-70-6 Synthesis

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