N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine

Base Information

• Chemical Name: N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine
• CAS No.: 480432-14-2
• Molecular Formula: C19H25NO
• Molecular Weight: 283.414
• UNII: 956HC7TAM9
• DSSTox Substance ID: DTXSID60431896
• Nikkaji Number: J1.208.251G
• Mol file: 480432-14-2.mol

Synonyms:480432-14-2;rac Desisopropyl Tolterodine;N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine;4-methyl-2-[1-phenyl-3-(propan-2-ylamino)propyl]phenol;956HC7TAM9;rac Desisopropyl Tolterodine-d7;UNII-956HC7TAM9;Tolterodine tartrate impurity E [EP];4-Methyl-2-((1RS)-3-((1-methylethyl)amino)-1-phenylpropyl)phenol;Phenol, 4-methyl-2-(3-((1-methylethyl)amino)-1-phenylpropyl)-;4-Methyl-2-[(1RS)-3-[(1-methylethyl)amino]-1-phenylpropyl]phenol ((RS)-Desisopropyltolterodine);2-[3-(Isopropylamino)-1-phenylpropyl]-4-methylphenol;Tolterodine impurity E;SCHEMBL579694;2-(3-Isopropylamino-1-phenyl-propyl)-4-methyl-phenol;DTXSID60431896;AKOS030254692;FT-0666043;FT-0666044;4-Methyl-2-[1-phenyl-3-(isopropylamino)propyl]phenol;TOLTERODINE TARTRATE IMPURITY E [EP IMPURITY];4-methyl-2-{1-phenyl-3-[(propan-2-yl)amino]propyl}phenol;Phenol, 4-methyl-2-[3-[(1-methylethyl)amino]-1-phenylpropyl]-;4-Methyl-2-[(1RS)-3-[(1-methylethyl)amino]-1-phenylpropyl]phenol;Tolterodine Tartrate Imp. E (EP);Tolterodine Tartrate Impurity E;Tolterodine Impurity E

Chemical Property of N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine

Chemical Property:

• Boiling Point: 426.9±45.0 °C(Predicted)
• PKA: 10.13±0.48(Predicted)
• PSA: 32.26000
• Density: 1.026±0.06 g/cm3(Predicted)
• LogP: 4.61150
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 283.193614421
• Heavy Atom Count: 21
• Complexity: 285

Purity/Quality:

95%-98% ^*data from raw suppliers

rac Desisopropyl Tolterodine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)O)C(CCNC(C)C)C2=CC=CC=C2
• Uses: As a metabolite of Tolterodine (T535800), ac Desisopropyl Tolterodine can be used in the treatment of smooth muscle hyperactivity.

Technology Process of N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine

There total 5 articles about N-Isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine 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: 89.0%

N-isopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropylamine (854306-69-7) → N-isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine (480432-14-2)

Guidance literature:

With hydrogen; In methanol; at 25 - 30 ℃; under 2625.26 Torr; Autoclave;

DOI:10.1021/op050024w

Reference yield:

methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate (854306-67-5) → N-isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine (480432-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 25 - 35 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 35 °C

3: acetonitrile / 12 h / 35 - 40 °C

4: hydrogen / methanol / 25 - 30 °C / 2625.26 Torr / Autoclave

With hydrogen; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/op050024w

Reference yield:

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol (854306-68-6) → N-isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine (480432-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 35 °C

2: acetonitrile / 12 h / 35 - 40 °C

3: hydrogen / methanol / 25 - 30 °C / 2625.26 Torr / Autoclave

With hydrogen; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/op050024w

upstream raw materials:

N-isopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropylamine

Cinnamic acid

methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol

Downstream raw materials:

N-(3-(2-(benzyloxy)-5-methylphenyl)-3-phenylpropyl)-N-isopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropan-1-amine

bis{4-methyl-2-(3-phenylpropyl)phenol}