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With hydrogenchloride; In diethyl ether; ethyl acetate;
To a solution OF 7-METHOXY-3, 4-DIHYDRO-2H-ISOQUINOLIN-1-ONE (200mg) in THF (8mL) is added LiAIH4 (76mg) and stirred for 3hr under reflux, and diluted with THF. The reaction mixture is added sodium sulfate decahydrate and filtration through celite pad. The filtrate is concentrated in vacuo. The residue is dissolved in Et20, then HCI in EtOAc is added the Et20. White precipitate is collected. by filtration to provide the title compound; 1 H NMR (CDCI3, 6 (ppm) ); 2.92 (dd, 2H), 3.30-3. 35 (m, 2H), 3.72 (s, 3H), 4.18-4. 23 (m, 2H), 6.81- 6.86 (m, 2H), 7.12 (d, 1H), 9.45 (brs, 2H).
With hydrogenchloride; In diethyl ether; ethyl acetate;
Lithium aluminium hydride, L. OM solution in THF (Aldrich, 21,277-6) (22mL, 22MMOL) was added drop wise to 7-METHOXY-3, 4-dihydro-2H-isoquinolin-l-one (3. 0g, 17MMOL) in THF (25mL) at RT. After addition the reaction was refluxed for 3HRS. THE reaction was cooled to 0C and quenched by the careful addition of deionised H20 (1ML), 10% OH solution (LML) and deionised H20 (3mL). The basic suspension was filtered through celite and extracted into EtOAc (3XL50ML). The combined extracts were dried over MGS04 and the solvent was removed in vacuo. The residue was purified via flash chromatography eluting with MEOH/CH2CL2 (10: 90) to AFFORD 7-METHOXY-1, 2, 3,4-tetrahydro-isoquinoline. This was dissolved in EtOAc (LOML) and hydrogen chloride, 2. 0m solution in Et2O (Aldrich, 45,518-0) (lOmL) was added drop wise, which formed a white ppte. The solid was filtered off and washed with Et20 to afford 7-methoxy-1,2, 3, 4-TETRALLYDRO- isoquinoline hydrochloride as a white solid. Yield 1.4g (42%). HPLC retention time, 3. 05min. Mass spectrum (ES+) m/z 164 (M + H).
7-Methoxy-3.4-dihydro-1H-isoquinoline-2-sulfonyl chloride[ No CAS ]
7-Methoxy-3.4-dihydro-1H-isoquinoline-2-sulfonic acid [1-(4-amino-thieno[3,2-c]pyridin-2-ylmethyl)-2-(4-methyl-piperidin-1-vi)-2-oxo-ethyl]-amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sulfuryl dichloride; triethylamine; In diethyl ether; chloroform;
63f. 7-Methoxy-3.4-dihydro-1H-isoquinoline-2-sulfonyl chloride To a stirred, precooled solution (-40 C.) of 0.41 mL of sulfuryl chloride in 10 mL of chloroform was added a mixture of 1.0 g of <strong>[1745-05-7]7-methoxy-1,2,3,4-tetrahydro-isoquinoline-hydrochloride</strong> and 2.1 mL of triethylamine in 25 mL of chloroform at -40 C. Stirring was continued at -30 C. for one hour and additionally at 5 C. for one hour. The mixture was poured on ice, the organic layer extracted with cold water, dried (sodium sulfate) and concentrated. The residue was redissolved in diethyl ether and chromatographed on silica gel (isohexane/ethyl acetate=8/2 v/v) yielding 0.62 g of 7-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride as an oil. EI-MS: 261 (M+).
N-(3,3-diphenyl-propyl)-2-(7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
36%
-METHOXY-1, 2,3, 4-tetrahydro-isoquinoline hydrochloride (200mg, lmmol) was stirred in MECN (lOmL) with K2CO3 (276mg, 2mmol) and TBAI (Aldrich, 14,077- 5) (74mg, 0. 2MMOL) for 30mins. 2-CHLORO-N- (3, 3-DIPHENYL-PROPYL)-ACETAMIDE (288MG, I MMOL) was added and the reaction was refluxed for 24hrs. The reaction was cooled, diluted with MECN (LOML) and the insoluble material was removed via filtration. The solvent was removed in vacuo and the residue was purified via flash chromatography eluting with EtoAc/isohexane (1: 4) to afford the title compound as an orange oil. Yield 150mg (36%) HPLC retention time, 4. 45MIN. Mass spectrum (ES+) m/z 415 (M + H).
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