5-(3-CHLORO-PROPYL)-10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPINE synthesis
- 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
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Yield:16036-79-6 40%
Reaction Conditions:
Stage #1: 9,10-dihydrodibenz
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
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109-70-6
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![5-(2-Propenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine](/CAS/GIF/74074-21-8.gif)
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16036-79-6
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![3-CHLORO-1-(10,11-DIHYDRO-DIBENZO[B,F]AZEPIN-5-YL)-PROPAN-1-ONE](/CAS/GIF/19054-67-2.gif)
19054-67-2
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16036-79-6
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494-19-9
339 suppliers
$6.00/25g
16036-79-6
14 suppliers
$95.00/5mg