1,1-Dimethylethyl 4-(aminocarbonyl)-4-[(2-phenylethyl)amino]-1-piperidinecarboxylate

Base Information

• Chemical Name: 1,1-Dimethylethyl 4-(aminocarbonyl)-4-[(2-phenylethyl)amino]-1-piperidinecarboxylate
• CAS No.: 288154-19-8
• Molecular Formula: C₁₉H₂₉N₃O₃
• Molecular Weight: 347.458
• DSSTox Substance ID: DTXSID501128545
• Mol file: 288154-19-8.mol

Synonyms:DTXSID501128545;1,1-Dimethylethyl 4-(aminocarbonyl)-4-[(2-phenylethyl)amino]-1-piperidinecarboxylate;288154-19-8

Chemical Property of 1,1-Dimethylethyl 4-(aminocarbonyl)-4-[(2-phenylethyl)amino]-1-piperidinecarboxylate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 347.22089180
• Heavy Atom Count: 25
• Complexity: 459

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(CC1)(C(=O)N)NCCC2=CC=CC=C2

Technology Process of 1,1-Dimethylethyl 4-(aminocarbonyl)-4-[(2-phenylethyl)amino]-1-piperidinecarboxylate

There total 4 articles about 1,1-Dimethylethyl 4-(aminocarbonyl)-4-[(2-phenylethyl)amino]-1-piperidinecarboxylate 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: 62.0%

phenylacetaldehyde (122-78-1) + tert-butyl 4-amino-4-carbamoylpiperidine-1-carboxylate (288154-18-7) → 1-Boc-4-[(2-phenylethyl)amino]piperidine-4-carboxamide (288154-19-8)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 1h;

DOI:10.1021/jm990962k

Reference yield:

4-(Benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-piperidine-4-carboxylic Acid (288154-16-5) → 1-Boc-4-[(2-phenylethyl)amino]piperidine-4-carboxamide (288154-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NMM / 1,2-dimethoxy-ethane / 0.08 h / -15 °C

2: aq. NH₃ / 1,2-dimethoxy-ethane / 1 h / 20 °C

3: 100 percent / aq. HCl / 10percent Pd/C / ethanol / 20 °C

4: 62 percent / NaBH₃CN; AcOH / methanol / 1 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; ammonium hydroxide; sodium cyanoborohydride; acetic acid; 10percent Pd/C; In methanol; 1,2-dimethoxyethane; ethanol; 1: Acylation / 2: ammonolysis / 3: Hydrogenolysis / 4: reductive amination;

DOI:10.1021/jm990962k

Reference yield:

1-Boc-4-[Z-amino]piperidine-4-carboxamide (288154-17-6) → 1-Boc-4-[(2-phenylethyl)amino]piperidine-4-carboxamide (288154-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / aq. HCl / 10percent Pd/C / ethanol / 20 °C

2: 62 percent / NaBH₃CN; AcOH / methanol / 1 h / 20 °C

With hydrogenchloride; sodium cyanoborohydride; acetic acid; 10percent Pd/C; In methanol; ethanol; 1: Hydrogenolysis / 2: reductive amination;

DOI:10.1021/jm990962k

upstream raw materials:

phenylacetaldehyde

tert-butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

4-(Benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-piperidine-4-carboxylic Acid

1-Boc-4-[Z-amino]piperidine-4-carboxamide

Downstream raw materials:

1-(2-phenylethyl)-8-Boc-1,3,8-triazaspiro[4.5]dec-2-en-4-one

1-(2-phenylethyl)-8-Boc-1,3,8-triazaspiro[4.5]decan-4-one-3-acetic acid

1-(2-phenylethyl)-8-Boc-1,3,8-triazaspiro[4.5]decan-4-one