{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

Base Information

Chemical Name:{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine
CAS No.:51934-13-5
Molecular Formula:C₂₀H₂₆N₂O₂
Molecular Weight:326.439
Hs Code.:

Synonyms:{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

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Chemical Property of {2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

Chemical Property:

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Technology Process of {2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

There total 24 articles about {2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-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: 94.0%

: 216006-00-7
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

: 51934-13-5
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

Guidance literature:: With potassium hydroxide; In ethanol; for 36h; Heating;
DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

: 27124-93-2
1-(3,4-dimethoxyphenyl)cyclohexene

: 51934-13-5
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

Guidance literature:: Multi-step reaction with 19 steps

1: 90 percent / AD-mix-α, K2CO3, K3Fe(CN)6, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / Ambient temperature

2: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

3: 98 percent / Et₃NSO₂NCO₂Me / toluene / 1 h / 50 °C

4: 98 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

5: 98 percent / NBS / diethyl ether / 24 h / 0 °C / to RT

6: 87 percent / Bu₃SnCl, AIBN, NaBH₄ / 2-methyl-propan-2-ol / 6 h / Heating

7: 93 percent / mCPBA, BF₃*OEt₂ / CH₂Cl₂ / 1 h / Ambient temperature

8: 98 percent / Me₃Al / tetrahydrofuran / 8 h / Heating

9: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C

10: LiAlH₄ / tetrahydrofuran / 48 h / Heating

11: Et₃N / CH₂Cl₂ / Ambient temperature

12: 91 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

13: 82 percent / various solvent(s) / 18 h / Heating

14: 73 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 2 h / -15 °C

15: 88 percent / I₂ / pyridine; CCl₄ / 20 h / Ambient temperature

16: 95 percent / i-Pr₂NH / PdCl₂(PPh₃)2, CuI / tetrahydrofuran / 0.67 h / 0 °C

17: 98 percent / H₂ / Lindlar catalyst / ethyl acetate / 3 h / Ambient temperature

18: 76 percent / NH₄OAc / acetic acid / 24 h / 100 °C

19: 94 percent / KOH / ethanol / 36 h / Heating

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; potassium hydroxide; sodium tetrahydroborate; AD-mix-α; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; Burgess Reagent; 2,2'-azobis(isobutyronitrile); methanesulfonamide; boron trifluoride diethyl etherate; tributyltin chloride; ammonium acetate; hydrogen; iodine; trimethylaluminum; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; copper(l) iodide; In tetrahydrofuran; pyridine; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

: 216005-90-2
{2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2-hydroxy-cyclohexyl]-ethyl}-methyl-carbamic acid methyl ester

: 51934-13-5
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

2: 82 percent / various solvent(s) / 18 h / Heating

3: 73 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 2 h / -15 °C

4: 88 percent / I₂ / pyridine; CCl₄ / 20 h / Ambient temperature

5: 95 percent / i-Pr₂NH / PdCl₂(PPh₃)2, CuI / tetrahydrofuran / 0.67 h / 0 °C

6: 98 percent / H₂ / Lindlar catalyst / ethyl acetate / 3 h / Ambient temperature

7: 76 percent / NH₄OAc / acetic acid / 24 h / 100 °C

8: 94 percent / KOH / ethanol / 36 h / Heating

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium hydroxide; ammonium acetate; hydrogen; iodine; sodium hydride; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; copper(l) iodide; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; dichloromethane; acetic acid; ethyl acetate;
DOI:10.1016/S0040-4039(98)01689-X