C₁₄H₁₉ON

Base Information

• Chemical Name: C₁₄H₁₉ON
• CAS No.: 220503-22-0
• Molecular Formula: C₁₄H₁₉NO
• Molecular Weight: 217.311
• Mol file: 220503-22-0.mol

Synonyms:C₁₄H₁₉ON

Chemical Property of C₁₄H₁₉ON

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₄H₁₉ON

There total 10 articles about C₁₄H₁₉ON 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:

C9H16NO3SBr (951240-63-4) → C14H19ON (220503-22-0)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2: CuBr*SMe₂ / tetrahydrofuran; diethyl ether / -40 - -35 °C

3: sodium carbonate / Pd(Ph₃P)4 / ethanol; toluene; H₂O / 0.75 h / 80 °C

4: anisole; triflic acid / CH₂Cl₂ / 0.5 h / 0 °C

5: sodium cyanoborohydride / acetonitrile; H₂O / 0.5 h

With dmap; copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; sodium cyanoborohydride; sodium carbonate; methoxybenzene; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; 2: Grignard reaction / 3: Suzuki coupling;

DOI:10.1021/ol0713988

Reference yield:

C13H25NO6SBrP (951240-64-5) → C14H19ON (220503-22-0)

Guidance literature:

Multi-step reaction with 4 steps

1: CuBr*SMe₂ / tetrahydrofuran; diethyl ether / -40 - -35 °C

2: sodium carbonate / Pd(Ph₃P)4 / ethanol; toluene; H₂O / 0.75 h / 80 °C

3: anisole; triflic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: sodium cyanoborohydride / acetonitrile; H₂O / 0.5 h

With copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; sodium cyanoborohydride; sodium carbonate; methoxybenzene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; 1: Grignard reaction / 2: Suzuki coupling;

DOI:10.1021/ol0713988

Reference yield:

C9H15NO4S → C14H19ON (220503-22-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.68 g / triethylsilane; BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 °C

2: bromine / CH₂Cl₂ / 0.5 h / 0 °C

3: 0.73 g / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

4: (R)-1-Me-3,3-Ph-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane-N,N-diethylaniline complex / tetrahydrofuran / 16 h / 0 - 20 °C

5: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

6: CuBr*SMe₂ / tetrahydrofuran; diethyl ether / -40 - -35 °C

7: sodium carbonate / Pd(Ph₃P)4 / ethanol; toluene; H₂O / 0.75 h / 80 °C

8: anisole; triflic acid / CH₂Cl₂ / 0.5 h / 0 °C

9: sodium cyanoborohydride / acetonitrile; H₂O / 0.5 h

With triethylsilane; dmap; borane N,N-diethylaniline complex; copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; bromine; sodium cyanoborohydride; sodium carbonate; methoxybenzene; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; 6: Grignard reaction / 7: Suzuki coupling;

DOI:10.1021/ol0713988

upstream raw materials:

C₁₃H₁₇ON

formaldehyd

C₉H₁₆NO₃SBr

C₁₃H₂₅NO₆SBrP

Downstream raw materials:

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol

(3R,4R)-4-(3-methoxyphenyl)-3,4-dimethylpiperidine

(+)-1,3(R),4(R)-Trimethyl-4-(3-methoxyphenyl)piperidine

Refernces