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CAS No. : | 40432-52-8 | MDL No. : | MFCD03093386 |
Formula : | C16H18N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LYTNNHXGUOKXFI-UHFFFAOYSA-N |
M.W : | 238.33 | Pubchem ID : | 5744546 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With hydrogen In ethyl acetate for 15 h; | [Referential Example 105] ;3-Amino-1-benzhydrylazetidine ; [] 5percent Palladium-carbon (200 mg) was added to 3-azido-1-benzhydrylazetidine (630 mg) obtained from Referential Example 104 in ethyl acetate (12 mL). The resultant mixture was subjected to catalytic reduction in a hydrogen atmosphere for 15 hours. The catalyst was filtered off. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform - methanol), to thereby give the title compound as a solid (410 mg, 65percent).1H-NMR(400MHz,CDCl3)δ: 1.45(2H,br), 2.62-2.67(2H,m), 3.51-3.54(2H,m), 3.59-3.66(1H,m), 4.28(1H,s), 7.16-7.40(10H,m) . LC-MSm/z: 239(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.3% | With hydrazine hydrate In methanol; diethyl ether | EXAMPLE 2 A mixture of 0.244 mol of 1-benzhydryl-3-phthalimidoazetidine in 1000 ml of anhydrous methanol is heated at reflux for 15 minutes, then, after removing the heating bath, 0.339 mol of 85percent hydrazine hydrate are added thereto. The mixture is heated at reflux for 30 minutes, then a solid white product begins to precipitate from the limpid solution thus obtained. The mixture is again heated for 90 minutes, then it is cooled at 10° C. One liter of diethyl ether is added to the mixture which is then filtered. After washing with ether, the solid product (35 g) is discarded and the mother-liquor is concentrated under reduced pressure. The residue is taken up with 500 ml of water and the pH of the solution is adjusted to 11 with sodium hydroxide. After extraction with 1 liter of diethyl ether, the ethereal phase is washed with water, dried on anhydrous sodium sulfate and evaporated under reduced pressure. Thus, the 3-amino-1-benzhydrylazetidine is obtained in the form of an oil which tends to solidify Yield 96.3percent. |
89% | With methylamine In ethanol; water at 20℃; for 168 h; | EXAMPLE A333-amino-1-(diphenylmethyl)-azetidine572 ml of 40percent aqueous methylamine solution and 300 ml of water were added successively to a suspension of 78.0 g (0.212 mol) of 1-(diphenylmethyl)-3-(phthalimido)-azetidine in 480 ml of ethanol. After 7 days' stirring at ambient temperature a clear solution had formed, which was freed from excess methylamine and ethanol in vacuo. The aqueous solution remaining was extracted exhaustively with ethyl acetate. The ethyl acetate extracts were dried over sodium sulphate and dried in vacuo. 45.0 g (89percent of theoretical) of a colourless oil were obtained, which was further processed without any additional purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonia In methanol | A. 1-Benzhydryl-azetidin-3-ylamine Ammonia gas was bubbled through a solution of methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (952.4 mg, 3 mmol) in MeOH (15 mL). After 2 hours, TLC showed the reaction to be complete. The title compound was obtained as a white solid (643.5 mg, 90percent) after removal of the solvent. MS: 239 (MH+); HPLC Rf: 3.54 min; HPLC purity: 98percent. |
84% | With ammonia In water; isopropyl alcohol at 50 - 71℃; for 3 h; | Preparation of Formula IV; The mesylate wet cake (838 g dry weight expected, 2.64 mol) (Example 1) was dissolved in isopropanol at 50°C. The solution was charged to a 2 gallon Parr reactor, followed by the addition of 28 wtpercent ammonium hydroxide under vacuum (10 vol of 28percent NH4OH and 15 vol of isopropanol). The Parr reactor was sealed, and heated to 71 °C for 3 h (38 - 40 psi pressure observed). The reaction was assayed by HPLC, and showed reaction completion. The reaction mixture was cooled to room temperature, discharged from the Parr reactor, and concentrated under vacuum. The product was extracted with isopropyl ether (8.4 L). The organic extract was concentrated to ~ 4 L under atmospheric pressure, and 159 g (1 eq.) of acetic acid was added, the mixture was stirred for 2 h, and the product (mono acetate salt) was collected by filtration. The solids were dried at 4O0C under vacuum to give 662 g of product (84percent yield). About 4percent of the Formula IV dimer was observed. 1H NMR (CD3OD, 400 MHz) 7.42-7.04 (m, 10 H), 4.44 (s, 1 H), 3.78-3.62 (m, 1 H), 3.43-2.36 (m, 2H), 3.03-2.99 (m, 2H), 1.93 (s, 3H). 13C NMR (CD3OD, 100 MHz) 176.2, 141.4, 128.3, 127.3, 127.2, 77.5, 58.3, 41.2, 22.2. |
70% | With ammonia In methanol; water; isopropyl alcohol at 70 - 75℃; for 3 h; | Example 3: Preparation of Formula IV; The reaction conditions were similar to Example 2, except that 10 volumes 7N ammonia in methanol was added under vacuum to 15 volumes isopropanol. The reaction was heated to 70-750C resulting in a pressure of 40-50 psi. After three hours, the reaction was nearly complete with a ratio of IV to its dimer of 94:6 by HPLC. The product was isolated by evaporation and recrystallized from isopropyl ether to give a 70percent yield. |
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