Structure of 625437-38-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 625437-38-9 |
Formula : | C12H17N |
M.W : | 175.27 |
SMILES Code : | CC1=C(C)C(CNC2CC2)=CC=C1 |
MDL No. : | MFCD11204718 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
* 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 |
---|---|---|
95% | Methanol (70OmL), sodium bicarbonate (43.4 g, 516 mmol), <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> (46.2g, 344 mmol), and cyclopropylamine (29 mL, 413 mmol) were combined. The mixture was heated to 67 0C for 30 min. The mixture was cooled to 5 0C and sodium borohydride (15.6 g. 413 mmol) was added in portions to keep temperature below 20 0C. Once addition was completed, the reaction mixture was concentrated to remove MeOH. The white residue was taken up in 50OmL CH2Cb and 50OmL water. Water layer was cut and organic layer was washed twice with 50OmL Na2CO3 10percent aq., then dried over MgSO4. Organics were concentrated to give a colorless oil. The oil was dissolved in 500 mL MTBE and stirred at 5 0C as HCl in Et2O (189 mL of 2 N) was added slowly. After addition was complete, solids were filtered off and washed with MTBE. Solids were dried under vacuum to give 57.36g (79percent yield) of a white solid.; Preparation of 2,3-Dimethylbenzylamine 1 1-4:<strong>[5779-93-1]2,3-Dimethylbenzaldehyde</strong> (16.14 g, 120 mmol) was added to a mixture OfNaHCO3 (15.2 g, 180 mmol) and cyclopropylamine (8.24 g, 144 mmol) in MeOH (32 mL) and the resulting suspension was refluxed for 4 h, then cooled to 0 0C. NaBH4 (5.46 g, 144 mmol) was added portion-wise and the mixture was aged 18 h. The mixture was concentrated and partitioned between CH2Cl2 (100 mL) and water (200 mL). The organic layer was washed with brine (100 mL), filtered through cotton and <n="54"/>concentrated. The residue assayed at 20 g (95percent). The material was dissolved in Et2O (200 mL) and 2N HCl (1.1 equiv) was added. The resulting suspension was filtered to afford 20.5 g of white solid HCl salt of the desired amine UA- 1H NMR (400 MHz, DMSO): delta 9.23 (s, 2H), 7.31 (d, IH), 7.20 (d, IH), 7.13 (t, IH), 4.22 (s, 2H), 2.71 (s, IH), 2.26 (d, 5H), 0.90 (s, 2H), 0.79-0.73 (m, 2H). | |
87% | Cyclopr opyl-(2,3-dimethylbenzyl)amine (11); EPO <DP n="18"/>A mixture of 2,3-dichlorobenzaldehyde (68.9 g, 514 mmol) and cyclopropylamine (72 mL, 1.02 mol) in dry MeOH (1300 mL) was stirred at rt overnight. The reaction mixture was cooled to 0 °C, and NaBH4 (25.3 g, 668 mmol) was added. The reaction mixture was stirred again at rt overnight. Ice was added to the reaction mixture, and the solvents were evaporated under reduced pressure. The residue was dissolved in EtOAc, and was washed with aq. IM NaOH. The aq. layer was extracted with EtOAc (3x). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc / heptane 9:1 - > 1:1) yielded the title compound (78.4 g, 87percent). LC-MS: tR = 0.84 min; ES+: 176.13. | |
Amine 1N-(2,3-Dimethylbenzyl)cyclopropanamineA mixture of <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> (1 eq.), cyclopropylamine (1.2 eq.) and sodium bicarbonate (1.5 eq.) were heated at reflux in MeOH (0.5 M) for 1 h. The reaction mixture was then cooled in ice and sodium borohydride (1.2 eq.) was introduced portionwise. Following the completion of addition, the reaction mixture was warmed to RT and stirred at RT for 1 h. The volatiles were then removed in vacuo and the resulting residue was partitioned between H2O and CH2Cl2. The organic layer was separated, washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a light yellow oil |
Tags: 625437-38-9 synthesis path| 625437-38-9 SDS| 625437-38-9 COA| 625437-38-9 purity| 625437-38-9 application| 625437-38-9 NMR| 625437-38-9 COA| 625437-38-9 structure
A189715 [909702-86-9]
N-(2,3-Dimethylbenzyl)cyclopropanamine hydrochloride
Reason: Free-salt
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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