No renderable structure data available
CC(C)(C)OC(=O)N1CCN(CC1)CCC2=CC(=CC=C2)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 4-[2-(3-aminophenyl)ethyl]piperazine-1-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 873697-82-6 |
| Database ID | 57597088 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 4-[2-(3-aminophenyl)ethyl]piperazine-1-carboxylate (CAS 873697-82-6) 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 57597088
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-f7a5ebebd5f740baa01b3dec111ed031Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-2b1147091ad64e86af5ddd7a8f6d1140Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2 SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%). The resulting reaction mixture the layers were separated The organic layer was washed twice with saturated aq. NaHCO3 and once with brine The organic layer was dried over Na2 SO4 filtered concentrated in vacuo Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant
Source ID: ord-fa341948b40c477aac7c6c4b77ca6cb0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/venting cycles with H2. The reaction mixture was allowed to proceed at room temperature and 45 psi H2 for 2.5 h. The reaction mixture was then charged with 12.5 wt eq of Pd(OH)2/C and the vessel was repressurized with hydrogen (45 psi). After 1 hr, the reaction mixture was filtered through a pad of diatomaceous earth, the diatomaceous earth washed with MeOH, and the combine organic layers concentrated in vacuo to provide the desired tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 63%), which was used without further purification. The reaction mixture was sealed in a Parr hydrogenation vessel to proceed at room temperature After 1 hr the reaction mixture was filtered through a pad of diatomaceous earth the diatomaceous earth washed with MeOH the combine organic layers concentrated in vacuo
Source ID: ord-1e1c025d7ab14121a00ff560c2b134d3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f7a5ebebd5f740baa01b3dec111ed031Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%). The resulting reaction mixture the layers were separated The organic layer was washed twice with saturated aq. NaHCO3 and once with brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant
Source ID: ord-52cddbaee2324b1dbb8c0cb3180ed7feConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/venting cycles with H2. The reaction mixture was allowed to proceed at room temperature and 45 psi H2 for 2.5 h. The reaction mixture was then charged with 12.5 wt eq of Pd(OH)2/C and the vessel was repressurized with hydrogen (45 psi). After 1 hr, the reaction mixture was filtered through a pad of diatomaceous earth, the diatomaceous earth washed with MeOH, and the combine organic layers concentrated in vacuo to provide the desired tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 63%), which was used without further purification. The reaction mixture was sealed in a Parr hydrogenation vessel to proceed at room temperature After 1 hr the reaction mixture was filtered through a pad of diatomaceous earth the diatomaceous earth washed with MeOH the combine organic layers concentrated in vacuo
Source ID: ord-307a610e647d4fb8b155bf525326ecedConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%). The resulting reaction mixture the layers were separated The organic layer was washed twice with saturated aq. NaHCO3 and once with brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant
Source ID: ord-6c31abf781f147269f653f35748dfa9dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/venting cycles with H2. The reaction mixture was allowed to proceed at room temperature and 45 psi H2 for 2.5 h. The reaction mixture was then charged with 12.5 wt eq of Pd(OH)2/C and the vessel was repressurized with hydrogen (45 psi). After 1 hr, the reaction mixture was filtered through a pad of diatomaceous earth, the diatomaceous earth washed with MeOH, and the combine organic layers concentrated in vacuo to provide the desired tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 63%), which was used without further purification. The reaction mixture was sealed in a Parr hydrogenation vessel to proceed at room temperature After 1 hr the reaction mixture was filtered through a pad of diatomaceous earth the diatomaceous earth washed with MeOH the combine organic layers concentrated in vacuo
Source ID: ord-c9e675cce62f4c5481e140432ff2b31aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2 SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%). The resulting reaction mixture the layers were separated The organic layer was washed twice with saturated aq. NaHCO3 and once with brine The organic layer was dried over Na2 SO4 filtered concentrated in vacuo Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant
Source ID: ord-fa341948b40c477aac7c6c4b77ca6cb0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/venting cycles with H2. The reaction mixture was allowed to proceed at room temperature and 45 psi H2 for 2.5 h. The reaction mixture was then charged with 12.5 wt eq of Pd(OH)2/C and the vessel was repressurized with hydrogen (45 psi). After 1 hr, the reaction mixture was filtered through a pad of diatomaceous earth, the diatomaceous earth washed with MeOH, and the combine organic layers concentrated in vacuo to provide the desired tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 63%), which was used without further purification. The reaction mixture was sealed in a Parr hydrogenation vessel to proceed at room temperature After 1 hr the reaction mixture was filtered through a pad of diatomaceous earth the diatomaceous earth washed with MeOH the combine organic layers concentrated in vacuo
Source ID: ord-1e1c025d7ab14121a00ff560c2b134d3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/venting cycles with H2. The reaction mixture was allowed to proceed at room temperature and 45 psi H2 for 2.5 h. The reaction mixture was then charged with 12.5 wt eq of Pd(OH)2/C and the vessel was repressurized with hydrogen (45 psi). After 1 hr, the reaction mixture was filtered through a pad of diatomaceous earth, the diatomaceous earth washed with MeOH, and the combine organic layers concentrated in vacuo to provide the desired tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 63%), which was used without further purification. The reaction mixture was sealed in a Parr hydrogenation vessel to proceed at room temperature After 1 hr the reaction mixture was filtered through a pad of diatomaceous earth the diatomaceous earth washed with MeOH the combine organic layers concentrated in vacuo
Source ID: ord-1e1c025d7ab14121a00ff560c2b134d3PubChem References
These sources are listed in the compound's public database record.
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