3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride

Base Information

• Chemical Name: 3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride
• CAS No.: 170842-81-6
• Molecular Formula: C15H21NO2.ClH
• Molecular Weight: 283.79400
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID10589972
• Mol file: 170842-81-6.mol

Synonyms:170842-81-6;3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride;3-Benzylpiperidine-3-carboxylic acid ethyl esterhydrochloride;3-Benzylpiperidine-3-ethylcarboxylate hydrochloride;Ethyl 3-benzylpiperidine-3-carboxylate hydrochloride;ETHYL 3-BENZYLPIPERIDINE-3-CARBOXYLATE HCL;ethyl 3-benzylpiperidine-3-carboxylate;hydrochloride;MFCD03840052;3-Benzylpiperidine-3-ethylcarboxylate, HCl;SCHEMBL8580878;DTXSID10589972;AR1301;AKOS005256915;AS-45082;DA-09386;CS-0172285;A881986;Ethyl3-benzylpiperidine-3-carboxylatehydrochloride;3-Benzylpiperidine-3-carboxylicacidethylesterhydrochloride;Ethyl 3-benzylpiperidine-3-carboxylate--hydrogen chloride (1/1);3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride, AldrichCPR

Chemical Property of 3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride

Chemical Property:

• Melting Point: 126-128°
• PSA: 38.33000
• LogP: 3.29280
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 283.1339066
• Heavy Atom Count: 19
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 3-benzylpiperidine-3-carboxylate hydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CCCNC1)CC2=CC=CC=C2.Cl

Technology Process of 3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride

There total 10 articles about 3-Benzylpiperidine-3-carboxylic acid ethyl ester hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

diethyl 2-benzyl-2-(2-cyanoethyl)malonate (10444-15-2) → (S)-3-carbethoxy-3-benzylpiperidine hydrochloride (170842-81-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / H₂, aq. HCl / Pd(OH)2 / ethanol / 22 h / 50 °C / 2172.02 Torr

2: 89 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

3: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

4: TFA / CH₂Cl₂ / 1.5 h / 40 °C

5: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

6: 93 percent / DMAP / toluene / 1 h / 60 °C

7: 90 percent / Superhydride / tetrahydrofuran / 2 h / 0 °C

8: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

9: HCl / CH₂Cl₂

With hydrogenchloride; triethylsilane; porcine liver esterase; dmap; phosphate buffer; boron trifluoride diethyl etherate; hydrogen; lithium triethylborohydride; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo980990v

Reference yield:

diethyl 2-benzylmalonate (607-81-8) → (S)-3-carbethoxy-3-benzylpiperidine hydrochloride (170842-81-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / EtONa, MTBE / ethanol / 1 h / 40 °C

2: 70 percent / H₂, aq. HCl / Pd(OH)2 / ethanol / 22 h / 50 °C / 2172.02 Torr

3: 89 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

4: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

5: TFA / CH₂Cl₂ / 1.5 h / 40 °C

6: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

7: 93 percent / DMAP / toluene / 1 h / 60 °C

8: 90 percent / Superhydride / tetrahydrofuran / 2 h / 0 °C

9: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

10: HCl / CH₂Cl₂

With hydrogenchloride; triethylsilane; porcine liver esterase; dmap; phosphate buffer; tert-butyl methyl ether; boron trifluoride diethyl etherate; hydrogen; sodium ethanolate; lithium triethylborohydride; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo980990v

Reference yield:

diethyl benzyl(3-N-Boc-aminopropyl)malonate (218434-83-4) → (S)-3-carbethoxy-3-benzylpiperidine hydrochloride (170842-81-6)

Guidance literature:

Multi-step reaction with 7 steps

1: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

2: TFA / CH₂Cl₂ / 1.5 h / 40 °C

3: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

4: 93 percent / DMAP / toluene / 1 h / 60 °C

5: 90 percent / Superhydride / tetrahydrofuran / 2 h / 0 °C

6: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

7: HCl / CH₂Cl₂

With hydrogenchloride; triethylsilane; porcine liver esterase; dmap; phosphate buffer; boron trifluoride diethyl etherate; lithium triethylborohydride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jo980990v

upstream raw materials:

3-benzyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

diethyl 2-benzyl-2-(2-cyanoethyl)malonate

diethyl 2-benzylmalonate

(S)-3-carbethoxy-3-benzyl-2-piperidone

Refernces