No renderable structure data available
COC(=O)C1CNCCN1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl piperazine-2-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 2758-98-7 |
| Database ID | 2760426 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl piperazine-2-carboxylate (CAS 2758-98-7) 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 2760426
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-588172bef07d435991b227960b066485Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-dcd3523db25d405b852ef93c1289d281Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-86ff8e28f847478998ed24da458369e0Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-588172bef07d435991b227960b066485Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Carbomethoxypiperazine was treated with benzyl chloroformate (1.0 eq) in aqueous NaHCO3 to give 1-benzyloxycarbonyl-3-carbomethoxypiperazine. This material was treated with di-tert-butyldicarbonate (1.1 eq) and triethylamine (1.0 eq) in THF to produce 1-tert-butyoxycarbonyl-4-benzyloxycarbonyl-2-carbomethoxypiperazine. Hydrogenation of this compound in methanol using 10% Pd—C gives the title compound after filtration and solvent removal.
Source ID: ord-e4636b6319e3412e988d77465204ca2bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was synthesized from methyl piperazine-2-carboxylate and 6-chloronicotinonitrile as described for example 39 step 1 (90 mg, yield 35%). 1H NMR (400 MHz, MeOD) δ 8.42 (dd, J=2.4 Hz, 0.6 Hz, 1H), 7.76 (dd, J=9.0 Hz, 2.3 Hz, 1H), 6.90 (m, 1H), 4.39-4.35 (dd, J=13.2 Hz, 2.6 Hz, 1H), 3.95-3.90 (m, 1H), 3.76 (s, 3H), 3.63-3.60 (dd, J=8.4 Hz, 3.4 Hz, 1H), 3.52-3.47 (dd, J=13.1 Hz, 8.4 Hz, 1H), 3.45-3.39 (ddd, J=13.1 Hz, 9.3 Hz, 3.4 Hz, 1H), 3.13-3.08 (m, 1H), 2.86-2.79 (ddd, J=12.5 Hz, 9.1 Hz, 3.5 Hz, 1H).
Source ID: ord-ce0191d4afb14ac78a61a3e170fd0c9dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: piperazine-2-carboxylic acid dihydrochloride (750 mg, 3.7 mmol) was suspended in MeOH (15 mL) and sodium bicarbonate (620 mg, 7.4 mmol) was added and stirred for 4 h. The reaction mixture was diluted with CH2Cl2 (15 mL) and cooled to 0° C. (Trimethylsilyl)diazomethane (15 mL, 2M in hexane) was added dropwise until the yellow color persisted. The solution was stirred at room temperature for 3 h and concentrated under reduced pressure. The crude product was purified by column chromatography (neutral alumina, eluent 5-6% MeOH in CHCl3) to get methyl piperazine-2-carboxylate (150 g, yield 28%). 1H NMR (300 MHz, CDCl3) δ 3.74 (s, 3H), 3.51-3.47 (dd, J=8.0 Hz, 3.4 Hz, 1H), 3.24-3.19 (dd, J=12.1 Hz, 3.3 Hz, 1H), 3.04-2.99 (m, 1H), 2.96-2.86 (m, 3H), 2.83-2.77 (m, 1H) was added dropwise until the yellow color The solution was stirred at room temperature for 3 h concentrated under reduced pressure The crude product was purified by column chromatography (neutral alumina, eluent 5-6% MeOH in CHCl3)
Source ID: ord-c87413698da04b4e97c5b50c78b1c9d0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Chloro-1-phenyl-1H-indole-3-carboxaldehyde is reacted with piperazine-2-carboxylic acid methyl ester as described in Example 1 to afford 4-(3-formyl-1-phenyl-1H-indole-2-yl)-piperazine-2-carboxylic acid methyl ester (9% yield) as a yellow solid. LC/MS: MS 364 (M+H); RT 2.54 min; NMR (CDCl3): 10.29 (1H, s), 8.26 (1H, d), 7.07-7.65 (m, buried), 6.98 (1H, d), 3.60-4.10 (4H, m), 2.60-3.55 (6H, m).
Source ID: ord-729c173c43c04ae48ce61ac5cde8916dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-86ff8e28f847478998ed24da458369e0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Carbomethoxypiperazine was treated with benzyl chloroformate (1.0 eq) in aqueous NaHCO3 to give 1-benzyloxycarbonyl-3-carbomethoxypiperazine. This material was treated with di-tert-butyldicarbonate (1.1 eq) and triethylamine (1.0 eq) in THF to produce 1-tert-butoxycarbonyl-4-benzyloxycarbonyl-2-carbomethoxypiperazine. Hydrogenation of this compound in methanol using 10% Pd—C gave the title compound after filtration and solvent removal.
Source ID: ord-1b21eacb71ac4914a80d95cc45e61477Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Chloro-1-phenyl-1H-indole-3-carboxaldehyde is reacted with piperazine-2-carboxylic acid methyl ester as described in Example 1 to afford 4-(3-formyl-1-phenyl-1H-indole-2-yl)-piperazine-2-carboxylic acid methyl ester (9% yield) as a yellow solid. LC/MS: MS 364 (M+H); RT 2.54 min; NMR (CDCl3): 10.29 (1H, s), 8.26 (1H, d), 7.07-7.65 (m, buried), 6.98 (1H, d), 3.60-4.10 (4H, m), 2.60-3.55 (6H, m).
Source ID: ord-d5d987f1f4684598a593f46a80613c3bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Carbomethoxypiperazine was treated with benzyl chloroformate (1.0 eq) in aqueous NaHCO3 to give 1-benzyloxycarbonyl-3-carbomethoxypiperazine. This material was treated with di-tert-butyldicarbonate (1.1 eq) and triethylamine (1.0 eq) in THF to produce 1-tert-butyoxycarbonyl-4-benzyloxycarbonyl-2-carbomethoxypiperazine. Hydrogenation of this compound in methanol using 10% Pd—C gives the title compound after filtration and solvent removal.
Source ID: ord-e4636b6319e3412e988d77465204ca2bPubChem References
These sources are listed in the compound's public database record.
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