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C#CCN1CCCCC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-prop-2-ynylpiperidine |
|---|---|
| IUPAC Name | — |
| CAS Number | 5799-75-7 |
| Database ID | 336652 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-prop-2-ynylpiperidine (CAS 5799-75-7) 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 336652
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-4b8a015f20754125b0c874fe8941651aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a5edd6fdbbbf4e528ebf7e468e21d804Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c96a83996b80489889f54ac2c8874e5aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5cbc2e1173a14d3fad78244abdd9d643Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using Method C above, 1-(2-propynyl)-piperidine (41.3 mg, 0.34 mmol) (prepared according to Kano et al. supra) was coupled with (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (Starting Material 3 supra) (50 mg, 0.135 mmol) using (Ph3P)4Pd (16 mg) and CuI (3 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 80° C. for 5 h to give (Z)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-4-[3-(1-pipendinyl)-1-propynyl]-2H-indol-2-one. (Yield 15 mg, 31%).
Source ID: ord-f55943094e4246edba6f5ba7dc2a396bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using Method C above, 1-(2-propynyl)-piperidine (41.3 mg, 0.34 mmol) (prepared according to Kano et al. supra) was coupled with (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (Starting Material 3 supra) (50 mg, 0.135 mmol) using (Ph3P)4Pd (16 mg) and Cul (3 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 80° C. for 5 h to give (Z)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-4-[3-(1-piperidinyl)-1-propynyl]-2H-indol-2-one. (Yield 15 mg, 31%).
Source ID: ord-995693fd9ee94bcd9859d64f75a6b4a4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4b8a015f20754125b0c874fe8941651aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using Method C above, 1-(2-propynyl)-piperidine (41.3 mg, 0.34 mmol) (prepared according to Kano et al. supra) was coupled with (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (Starting Material 3 supra) (50 mg, 0.135 mmol) using (Ph3P)4Pd (16 mg) and Cul (3 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 80° C. for 5 h to give (Z)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-4-[3-(1-piperidinyl)-1-propynyl]-2H-indol-2-one. (Yield 15 mg, 31%).
Source ID: ord-8a70ef200a5847c1b713b9c2ee28164cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using Method C above, 1-(2-propynyl)-piperidine (41.3 mg, 0.34 mmol) (prepared according to Kano et al. supra) was coupled with (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (Starting Material 3 supra) (50 mg, 0.135 mmol) using (Ph3P)4Pd (16 mg) and Cul (3 mg) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 80° C. for 5 h to give (Z)-1,3-dihydro-5-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-4-[3-(1-piperidinyl)-1-propynyl]-2H-indol-2-one. (Yield 15 mg, 31%).
Source ID: ord-8a70ef200a5847c1b713b9c2ee28164cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure described in example 43§C, but starting from 1-{3-[(4′-bromobiphenyl-4-yl)oxy]propyl}piperidine (0.75 g), 1-prop-2-yn-1-ylpiperidine (320 mg), triethylamine (20 mL), cuprous iodide (4.2 mg), triphenylphosphine (20 mg) and bis(triphenylphosphinepalladiumdichloride) affords 179 mg of 1-(3-{[4′-(3-piperidinoprop-1-yn-1-yl)biphenyl-4-yl]oxy}propyl)piperidine which oxalate melts at 195° C.
Source ID: ord-8ac4ff95480b4bbaaaf4254bd7871adaConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-prop-2-ynyl-piperidine (322 mg, 2.62 mmol), (4-{3-[3-bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (204 mg, 0.4 mmol, example 3), Pd(PPh3)4 (50 mg, 0.044 mmol), CuI (23 mg, 0.122 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 30 min at 60° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography using ethyl acetate/methanol mixtures to give (4-{3-[3,5-bis-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester in 138 mg (57%) yield. The reaction mixture was filtered through Decalite the filtrate was evaporated The residue was purified on column chromatography
Source ID: ord-b9470a8b9d4942029b7e8278df0e4b19Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-prop-2-ynyl-piperidine (322 mg, 2.62 mmol), (4-{3-[3-bromo-5-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (204 mg, 0.4 mmol, example 3), Pd(PPh3)4 (50 mg, 0.044 mmol), CuI (23 mg, 0.122 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 30 min at 60° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography using ethyl acetate/methanol mixtures to give (4-{3-[3,5-bis-(3-piperidin-1-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester in 138 mg (57%) yield. The reaction mixture was filtered through Decalite the filtrate was evaporated The residue was purified on column chromatography
Source ID: ord-b9470a8b9d4942029b7e8278df0e4b19PubChem References
These sources are listed in the compound's public database record.
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