5-(3-(4-(2,3-dichlorophenyl)piperidin-1-yl)propoxy)benzo[d]thiazole synthesis
- Product Name:5-(3-(4-(2,3-dichlorophenyl)piperidin-1-yl)propoxy)benzo[d]thiazole
- CAS Number:1354030-51-5
- Molecular formula:C21H22Cl2N2OS
- Molecular Weight:421.3832
Yield:1354030-51-5 56%
Reaction Conditions:
Stage #1: 5-(3-bromopropoxy)benzo[d]thiazolewith sodium iodide in acetonitrile; for 0.5 h;Reflux;
Stage #2: 4-(2,3-dichlorophenyl)piperidine hydrochloridewith potassium carbonate in acetonitrile;Reflux;
Steps:
22
Scheme 39. Synthesis of compound 22[0182] A mixture of intermediate 26 (218 mg, 0.8 mmol) and Nal (240 mg, 1.6 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 47 (320 mg, 1.2 mmol) and anhydrous K2C03 (442 mg, 3.8 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2S04, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH = 30: 1) to give 5-(3-(4-(2,3-dichlorophenyl)piperidin-l-yl)propoxy)benzo[d]thiazole (compound 22) (21 1 mg, 56%). NMR (300 MHz, CDC13): δ 8.98 (s, 1H), 7.80 (d, J = 8.7 Hz, 1H), 7.62 (d, J = 3.0 Hz, 1H), 7.34-7.31 (m, 1H), 7.24-7.18 (m, 3H), 7.15-7.09 (m, 1H), 4.15 (t, J = 5.7Hz, 2H), 3.18-3.12 (m, 3H), 2.70-2.66 (m, 2H), 2.27-2.19 (m, 2H), 2.17-2.10 (m, 2H), 1.92-1.81 (m, 4H). HPLC: 99%, RT 2.622 min. MS (ESI) m/z 421.1 [M + H]+. mp: 114-1 16°C.
References:
WO2012/3418,2012,A2 Location in patent:Page/Page column 77
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