4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 99633-72-4
• Molecular Formula: C₁₈H₁₉ClN₂O
• Molecular Weight: 314.815

Synonyms:4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

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Technology Process of 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline

There total 7 articles about 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline 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: 87.0%

nomifensine (24526-64-5) + chloroacetyl chloride (79-04-9) → 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline (99633-72-4)

Guidance literature:

With potassium carbonate; In acetone; for 0.5h; Heating;

Reference yield: 46.4%

2-Chloro-N-(2-{[(2-hydroxy-2-phenyl-ethyl)-methyl-amino]-methyl}-phenyl)-acetamide → 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline (99633-72-4)

Guidance literature:

With sulfuric acid; In dichloromethane; at 0 - 3 ℃; for 35h;

DOI:10.1021/jm00157a012

Reference yield:

(2-nitrobenzyl)methylamine (56222-08-3) → 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline (99633-72-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / triethylamine / diethyl ether / 4 h / 18 - 25 °C

2: 88 percent / NaBH₄ / methanol; H₂O / 4 h / Ambient temperature

3: 87 percent / H₂ / Raney nickel / ethanol / 12 h / 760 Torr

4: 4.2 g / pyridine / diethyl ether / 0.5 h / Ambient temperature

5: 46.4 percent / conc. H₂SO₄ / CH₂Cl₂ / 35 h / 0 - 3 °C

With pyridine; sodium tetrahydroborate; sulfuric acid; hydrogen; triethylamine; nickel; In methanol; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jm00157a012

upstream raw materials:

nomifensine

chloroacetyl chloride

(2-nitrobenzyl)methylamine

N-(2-Aminobenzyl)-2-(methylamino)-1-phenyl-1-ethanol

Downstream raw materials:

4-phenyl-2-methyl-8-piperidino-acetyl-amino-1,2,3,4-tetrahydro-isoquinoline

4-phenyl-2-methyl-8-morpholino-acetylamino-1,2,3,4-tetrahydro-isoquinoline

N-(2-Methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-2-(4-methyl-piperazin-1-yl)-acetamide

2-Dimethylamino-N-(2-methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinolin-8-yl)-acetamide

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