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CN1CC2CCC(C1)N2CC3=CC=CC=C3Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane |
|---|---|
| IUPAC Name | — |
| CAS Number | 57727-91-0 |
| Database ID | 21545507 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane (CAS 57727-91-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 21545507
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-004da3e18b5747279ed85d82a7c9735bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 6.1 g (0.019 mole) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione by the procedure employed to prepare 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane as related under Example 5 gave 4.9 g (88%) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane as a colorless oil.
Source ID: ord-05156878f65f4ecd98fbd8f0d1dbbed2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 6.1 g (0.019 mole) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione by the procedure employed to prepare 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane as related under Example 5 gave 4.9 g (88%) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane as a colorless oil.
Source ID: ord-05156878f65f4ecd98fbd8f0d1dbbed2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 8.2 g (0.038 mole) 8-benzyl-3-methyl-3,8-diazabicyclo [3.2.1]octane in 80 ml absolute ethanol containing 0.11 mole dry hydrogen chloride was hydrogenated in the presence of 1.5 g 10% palladium on charcoal at ambient temperature and pressure for 20 hours. The precipitated hydrochloride salt of the desired product was dissolved by addition of a little water, and, after filtration, the solvent was removed carefully in vacuo. The crystalline residue (6.9 g) was triturated with ethanol-diethyl ether containing dry hydrogen chloride to insure complete formation of the somewhat unstable dihydrochloride salt. Filtration gave 6.0 g (79%) of pure product, melting point 272°-280°C (dec.) with sublimation above 200°C.
Source ID: ord-b835e52b83bb43809cd821acc7f1186cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 8.2 g (0.038 mole) 8-benzyl-3-methyl-3,8-diazabicyclo [3.2.1]octane in 80 ml absolute ethanol containing 0.11 mole dry hydrogen chloride was hydrogenated in the presence of 1.5 g 10% palladium on charcoal at ambient temperature and pressure for 20 hours. The precipitated hydrochloride salt of the desired product was dissolved by addition of a little water, and, after filtration, the solvent was removed carefully in vacuo. The crystalline residue (6.9 g) was triturated with ethanol-diethyl ether containing dry hydrogen chloride to insure complete formation of the somewhat unstable dihydrochloride salt. Filtration gave 6.0 g (79%) of pure product, melting point 272°-280°C (dec.) with sublimation above 200°C.
Source ID: ord-b835e52b83bb43809cd821acc7f1186cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 9.6 g (0.039 mole) of 8-benzyl-3-methyl-3,8-diazabicyclo [3.2.1]octane-2,4-dione with lithium aluminum hydride in tetrahydrofuran by the procedure used for the preparation of 3-benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane, as described in Example 1, gave 8.3 g of crude desired product. Chromatography on 124 g alumina with chloroform elution gave 6.9 g (81%) of pure, oil 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane. The hydrochloride salt, formed in diethyl ether by addition of three equivalents of ethanolic hydrogen chloride, melted at 263.5°-272°C (dec.) with sublimation above 180°C. gave 8.3 g of crude desired product Chromatography on 124 g alumina with chloroform elution
Source ID: ord-b48c2ce293414c94b2f08f06814595dcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 9.6 g (0.039 mole) of 8-benzyl-3-methyl-3,8-diazabicyclo [3.2.1]octane-2,4-dione with lithium aluminum hydride in tetrahydrofuran by the procedure used for the preparation of 3-benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane, as described in Example 1, gave 8.3 g of crude desired product. Chromatography on 124 g alumina with chloroform elution gave 6.9 g (81%) of pure, oil 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane. The hydrochloride salt, formed in diethyl ether by addition of three equivalents of ethanolic hydrogen chloride, melted at 263.5°-272°C (dec.) with sublimation above 180°C. gave 8.3 g of crude desired product Chromatography on 124 g alumina with chloroform elution
Source ID: ord-b48c2ce293414c94b2f08f06814595dcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 6.1 g (0.019 mole) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione by the procedure employed to prepare 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane as related under Example 5 gave 4.9 g (88%) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane as a colorless oil.
Source ID: ord-05156878f65f4ecd98fbd8f0d1dbbed2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 6.1 g (0.019 mole) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione by the procedure employed to prepare 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane as related under Example 5 gave 4.9 g (88%) of 2,5-dibenzyl-2,5-diazabicyclo[2.2.2]octane as a colorless oil.
Source ID: ord-05156878f65f4ecd98fbd8f0d1dbbed2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 8.2 g (0.038 mole) 8-benzyl-3-methyl-3,8-diazabicyclo [3.2.1]octane in 80 ml absolute ethanol containing 0.11 mole dry hydrogen chloride was hydrogenated in the presence of 1.5 g 10% palladium on charcoal at ambient temperature and pressure for 20 hours. The precipitated hydrochloride salt of the desired product was dissolved by addition of a little water, and, after filtration, the solvent was removed carefully in vacuo. The crystalline residue (6.9 g) was triturated with ethanol-diethyl ether containing dry hydrogen chloride to insure complete formation of the somewhat unstable dihydrochloride salt. Filtration gave 6.0 g (79%) of pure product, melting point 272°-280°C (dec.) with sublimation above 200°C.
Source ID: ord-b835e52b83bb43809cd821acc7f1186cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reduction of 9.6 g (0.039 mole) of 8-benzyl-3-methyl-3,8-diazabicyclo [3.2.1]octane-2,4-dione with lithium aluminum hydride in tetrahydrofuran by the procedure used for the preparation of 3-benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane, as described in Example 1, gave 8.3 g of crude desired product. Chromatography on 124 g alumina with chloroform elution gave 6.9 g (81%) of pure, oil 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane. The hydrochloride salt, formed in diethyl ether by addition of three equivalents of ethanolic hydrogen chloride, melted at 263.5°-272°C (dec.) with sublimation above 180°C. gave 8.3 g of crude desired product Chromatography on 124 g alumina with chloroform elution
Source ID: ord-b48c2ce293414c94b2f08f06814595dcConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-004da3e18b5747279ed85d82a7c9735bPubChem References
These sources are listed in the compound's public database record.
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