Structure of 6240-01-3
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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. : | 6240-01-3 |
Formula : | C11H18ClNO2 |
M.W : | 231.72 |
SMILES Code : | O=C(C12CC3(N)CC(C2)CC(C3)C1)O.[H]Cl |
MDL No. : | MFCD01825827 |
InChI Key : | CMUAQGBJDDHTPE-UHFFFAOYSA-N |
Pubchem ID : | 365220 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
78% | With hydrogenchloride; water; at 95℃; for 144.0h; | Step 2: 3-Amino-adamantane-1-carboxylic acid hydrochloride; To a 3-neck 5-L flask equipped with a reflux condenser, a mechanical stirrer and a temperature probe was added 3-acetylamino-adamantane-1-carboxylic acid (432 g, 1.82 mol), water (1.00 L) and concentrated hydrochloric acid (2.44 L), and the resulting mixture was heated at 95 C. for 6 days. During this time, solid material precipitated from the solution. After cooling at 0 C., the solids were filtered and washed with acetone. The solid was then dried under high vacuum at 50 C. for about 2 hours to afford 328 g (78%) of the title compound, 3-amino-adamantane-1-carboxylic acid hydrochloride, as a white solid. 1H NMR (300 MHz, DMSO-td6) delta 12.35 (br s, 1H), 8.27 (br s, 3H), 2.22-2.12 (m, 2H), 1.92-1.85 (m, 2H), 1.83-1.71 (ml 6H), 1.69-1.48 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With thionyl chloride; at 60℃; | Step 3: 3-Amino-adamantane-1-carboxylic acid methyl ester hydrochloride; To a 3-neck 2-L flask equipped with a reflux condenser and a temperature probe was added <strong>[6240-01-3]3-amino-adamantane-1-carboxylic acid hydrochloride</strong> (100 g, 432 mmol) and methanol (1.0 L). To this solution was slowly added thionyl chloride (15.7 mL, 216 mmol) and the reaction was heated at 60 C. for 4 hours. Once cooled to room temperature, the crude reaction mixture was concentrated under reduced pressure to remove most of the methanol. Heptane (about 1-L) was then added and the mixture was once again concentrated under reduced pressure at which point a solid began to precipitate. This process was repeated three more times, then the solids were filtered off, washed with heptane and allowed to dry in open air to afford 97.2 g (92%) of the title compound, 3-amino-adamantane-1-carboxylic acid methyl ester hydrochloride, as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.46 (br s, 3H), 3.65 (s, 3H), 2.33-2.24 (m, 2H), 2.23-2.16 (m, 2H), 2.11-1.95 (m, 4H), 1.94-1.78 (m, 4H), 1.75-1.62 (m,2H). |
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