2-(4-(Benzyloxy)-3-methoxyphenyl)-N-methylethan-1-amine

Base Information

• Chemical Name: 2-(4-(Benzyloxy)-3-methoxyphenyl)-N-methylethan-1-amine
• CAS No.: 38171-33-4
• Molecular Formula: C17H21NO2
• Molecular Weight: 271.359
• DSSTox Substance ID: DTXSID80404027
• Wikidata: Q82207978
• Mol file: 38171-33-4.mol

Synonyms:38171-33-4;2-(4-(Benzyloxy)-3-methoxyphenyl)-N-methylethan-1-amine;Benzeneethanamine, 3-methoxy-N-methyl-4-(phenylmethoxy)-;2-[4-(Benzyloxy)-3-methoxyphenyl]-N-methylethan-1-amine;2-(3-methoxy-4-phenylmethoxyphenyl)-N-methylethanamine;4-BENZYLOXY-3-METHOXY-N-METHYLPHENETHYLAMINE;DTXSID80404027;AKOS022189473

Chemical Property of 2-(4-(Benzyloxy)-3-methoxyphenyl)-N-methylethan-1-amine

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 271.157228913
• Heavy Atom Count: 20
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CNCCC1=CC(=C(C=C1)OCC2=CC=CC=C2)OC

Technology Process of 2-(4-(Benzyloxy)-3-methoxyphenyl)-N-methylethan-1-amine

There total 13 articles about 2-(4-(Benzyloxy)-3-methoxyphenyl)-N-methylethan-1-amine 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: 67.0%

N-ethoxycarbonyl-4-benzyloxy-3-methoxyphenethylamine (1700-33-0) → 2-(4-(benzyloxy)-3-methoxyphenyl)-N-methylethanamine (38171-33-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere; Reflux;

DOI:10.1021/jo201056f

Reference yield:

N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]-N-(γ-chloropropyl)-amine + 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine (22231-61-4) + 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (1700-29-4) + isopropylamine (75-31-0) → 2-(4-(benzyloxy)-3-methoxyphenyl)-N-methylethanamine (38171-33-4)

Guidance literature:

With sodium hydroxide; ammonia; benzaldehyde; In N-methyl-acetamide; methanol; 2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamide oxalate; ethanol; dichloromethane; toluene;

Reference yield:

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) → 2-(4-(benzyloxy)-3-methoxyphenyl)-N-methylethanamine (38171-33-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / ammonium acetate / acetic acid / 1.5 h / Heating

2: LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 78 percent / 1 h / Heating

4: BF₃*OEt₂; BH₃*THF / tetrahydrofuran / 2 h / Heating

With ammonium acetate; lithium aluminium tetrahydride; borane-THF; boron trifluoride diethyl etherate; In tetrahydrofuran; acetic acid;

DOI:10.1055/s-2002-34844

upstream raw materials:

methyl iodide

N-formyl-2-[3-methoxy-4-(benzyloxy)phenyl]ethylamine

3-methoxy-4-(phenylmethoxy)benzaldehyde

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine

Downstream raw materials:

4-Hydroxy-3-methoxy-N-methylphenethylamine

N-ethoxycarbonyl-N-methyl-4-benzyloxy-3-methoxyphenethylamine

7-benzyloxy-3,4-dihydro-6-methoxy-2-methyl-2H-isoquinolin-1-one

(R)-1-(3-hydroxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline