Trans-4-(benzyloxy)cyclohexanamine

Base Information

• Chemical Name: Trans-4-(benzyloxy)cyclohexanamine
• CAS No.: 98454-39-8
• Molecular Formula: C13H19NO
• Molecular Weight: 205.29600
• DSSTox Substance ID: DTXSID50540789
• Mol file: 98454-39-8.mol

Synonyms:Trans-4-(benzyloxy)cyclohexanamine;98454-39-8;4-(benzyloxy)cyclohexanamine;cis-4-(Benzyloxy)cyclohexanamine;160357-83-5;98454-38-7;4-phenylmethoxycyclohexan-1-amine;Cyclohexanamine, 4-(phenylmethoxy)-, cis-;4-(Benzyloxy)cyclohexan-1-amine;Trans-4-(phenylMethoxy)cyclohexanaMine;starbld0018208;SCHEMBL1241681;SCHEMBL1241683;DTXSID50540789;AMY21458;AB8242;AB8243;MFCD14582896;MFCD14584854;MFCD14584855;AKOS012103695;AKOS023761728;SB77681;SB77993;AS-44218;AS-44883;CS-0312347;A934253

Chemical Property of Trans-4-(benzyloxy)cyclohexanamine

Chemical Property:

• PSA: 35.25000
• LogP: 3.17340
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 205.146664230
• Heavy Atom Count: 15
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

trans-4-(Benzyloxy)cyclohexanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CCC1N)OCC2=CC=CC=C2
• Uses: trans-4-(Benzyloxy)cyclohexanamine is a reactant used in the synthesis of the metabolites of Cilostazol (C441500), a potent phosphodiesterase III A (PDE3A) inhibitor (IC50=0.2uM) and inhibitor of adenosine uptake. Cilostazol (C441500) has antimitogeni, antithrombotic, vasodilatory and cardiotonic properties in vivo.

Technology Process of Trans-4-(benzyloxy)cyclohexanamine

There total 3 articles about Trans-4-(benzyloxy)cyclohexanamine 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: 83.0%

N-(trans-4-benzyloxycyclohexyl)acetamide (98454-33-2) → trans-O-benzyl-4-aminocyclohexanol (98454-39-8,160357-83-5)

Guidance literature:

With potassium hydroxide; In 2-methoxy-ethanol; water; for 20h; Heating;

DOI:10.1248/cpb.33.1140

Reference yield:

N-((trans)-4-hydroxycyclohexyl)acetamide (27489-60-7) → trans-O-benzyl-4-aminocyclohexanol (98454-39-8,160357-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / 60percent NaH, DMSO / 1 h / Ambient temperature

2: 83 percent / 85percent KOH / H₂O; 2-methoxy-ethanol / 20 h / Heating

With potassium hydroxide; sodium hydride; dimethyl sulfoxide; In 2-methoxy-ethanol; water;

DOI:10.1248/cpb.33.1140

Reference yield:

benzyl chloride (100-44-7) → trans-O-benzyl-4-aminocyclohexanol (98454-39-8,160357-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / 60percent NaH, DMSO / 1 h / Ambient temperature

2: 83 percent / 85percent KOH / H₂O; 2-methoxy-ethanol / 20 h / Heating

With potassium hydroxide; sodium hydride; dimethyl sulfoxide; In 2-methoxy-ethanol; water;

DOI:10.1248/cpb.33.1140

upstream raw materials:

N-(trans-4-benzyloxycyclohexyl)acetamide

N-((trans)-4-hydroxycyclohexyl)acetamide

benzyl chloride

Downstream raw materials:

N-(trans-4-benzyloxycyclohexyl)-5-chlorovaleramide

Refernces