No renderable structure data available
C1CCN(CC1)CCCC#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-piperidin-1-ylbutanenitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 4672-18-8 |
| Database ID | 78403 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-piperidin-1-ylbutanenitrile (CAS 4672-18-8) 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 78403
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7c598d8a8351422b8d097250aab2f4d2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e9543d8840f340f89f80e01f1efc75b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A process for the preparation of a compound of the formula ##STR25## which comprises (a) reacting 2-chlorobenzeneacetonitrile with 1-(2-chloroethyl)piperidine in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR26## (b) alkylating the resulting piperidinebenzene-butanenitrile with an alkylating agent in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR27## (c) hydrolyzing the resulting piperidine-butanenitrile in toluene with hydrochloric acid to produce a compound of the formula ##STR28## (d) reacting the resulting compound with isopropylamine in a solvent to form an imine of the formula ##STR29## (e) reducing the imine with sodium borohydride in ethanol to form an amine of the formula ##STR30## (f) acetylating the resulting amine with acetic anhydride in a solvent to produce an acetylated amine of the formula ##STR31## (g) hydrolyzing the acetylated amine with sulfuric acid to produce ##STR32## (h) recovering the compound so produced. A process for the preparation of a compound of the formula ##STR25## which
Source ID: ord-8a0d3c88ef6d4534849af2d89a1f5da0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A process for the preparation of a compound of the formula ##STR25## which comprises (a) reacting 2-chlorobenzeneacetonitrile with 1-(2-chloroethyl)piperidine in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR26## (b) alkylating the resulting piperidinebenzene-butanenitrile with an alkylating agent in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR27## (c) hydrolyzing the resulting piperidine-butanenitrile in toluene with hydrochloric acid to produce a compound of the formula ##STR28## (d) reacting the resulting compound with isopropylamine in a solvent to form an imine of the formula ##STR29## (e) reducing the imine with sodium borohydride in ethanol to form an amine of the formula ##STR30## (f) acetylating the resulting amine with acetic anhydride in a solvent to produce an acetylated amine of the formula ##STR31## (g) hydrolyzing the acetylated amine with sulfuric acid to produce ##STR32## (h) recovering the compound so produced. A process for the preparation of a compound of the formula ##STR25## which
Source ID: ord-8a0d3c88ef6d4534849af2d89a1f5da0Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7c598d8a8351422b8d097250aab2f4d2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e9543d8840f340f89f80e01f1efc75b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 10 mL oven-dried flask was added Mg turnings (97 mg, 4.1 mmol) which was activated by the use of a heat-gun under vacuum. Under inert atmosphere was added a suspension of 2-iodo-toluene (380 mL, 3.0 mmol) in Et2O (3 mL) and the reaction mixture was allowed to reflux for 1 hours. A suspension of 4-piperidin-1-yl-butanenitrile 10 (Dahlbom et. al. Acta. Chem. Scand. 1951, 5, 690-697) (0.305 mg, 2.0 mmol) in CH2Cl2 (3 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) and stirred at rt for 12 hours followed by addition of NaOH (12 mL, 2 M). Addition of THF (15 mL) was followed by extraction with ethyl acetate (3×50 mL), and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and dried (MgSO4) and evaporated to dryness to produce 0.21 g of crude 11. The crude product was subjected to preparative HPLC [eluent: Buffer A: 0.1% TFA; Buffer B: 80% CH3CN+0.1%TFA] to produce an analytically pure sample of compound 11; LC-MS [M+H]+ 245 (cald. 245.2). In a 10 mL oven-dried flask a heat-gun under vacuum Under inert atmosphere was added to reflux for 1 hours was added via a syringe The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) stirred at rt for 12 hours followed by addition of NaOH (12 mL, 2 M) Addition of THF (15 mL) was followed by extraction with ethyl acetate (3×50 mL) the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M) dried (MgSO4) evaporated to dryness to produce 0.21 g of crude 11
Source ID: ord-a118f632ccae42058a9d1b0a9fa0e2cdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using piperidine and 4-chloro-butanenitrile as substrates. MS (ion spray) m/z 153.
Source ID: ord-be19e17cbc344c33b18a23c37c850f82Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A process for the preparation of a compound of the formula ##STR25## which comprises (a) reacting 2-chlorobenzeneacetonitrile with 1-(2-chloroethyl)piperidine in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR26## (b) alkylating the resulting piperidinebenzene-butanenitrile with an alkylating agent in the presence of a base and DMSO to produce a piperidinebutanenitrile of the formula ##STR27## (c) hydrolyzing the resulting piperidine-butanenitrile in toluene with hydrochloric acid to produce a compound of the formula ##STR28## (d) reacting the resulting compound with isopropylamine in a solvent to form an imine of the formula ##STR29## (e) reducing the imine with sodium borohydride in ethanol to form an amine of the formula ##STR30## (f) acetylating the resulting amine with acetic anhydride in a solvent to produce an acetylated amine of the formula ##STR31## (g) hydrolyzing the acetylated amine with sulfuric acid to produce ##STR32## (h) recovering the compound so produced. A process for the preparation of a compound of the formula ##STR25## which
Source ID: ord-8a0d3c88ef6d4534849af2d89a1f5da0PubChem References
These sources are listed in the compound's public database record.
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