4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride

Base Information

• Chemical Name: 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride
• CAS No.: 1373215-42-9
• Molecular Formula: C₂₀H₂₂FN₃O₃*ClH
• Molecular Weight: 407.872
• Mol file: 1373215-42-9.mol

Synonyms:4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride

Chemical Property of 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride

There total 6 articles about 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride 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:

6-bromochroman-4-one (49660-57-3) → 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride (1373215-42-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tetrahydroborate / ethanol / 3 h / 20 °C / Industry scale

1.2: Industry scale; Cooling with ice

2.1: toluene-4-sulfonic acid / toluene / 3.83 h / 50 °C / Reflux; Industry scale

3.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C

4.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C

5.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C

5.2: 50 °C

6.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale

7.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere

7.2: pH 2.3

7.3: 1 h / 40 °C

With ammonium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; D-(+)-camphoric acid; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium t-butanolate; bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; isopropyl alcohol; toluene; acetonitrile;

Reference yield:

6-bromo-2H-benzopyran (18385-87-0) → 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride (1373215-42-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C

2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C

3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C

3.2: 50 °C

4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale

5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere

5.2: pH 2.3

5.3: 1 h / 40 °C

With ammonium hydroxide; N-Bromosuccinimide; D-(+)-camphoric acid; water; sodium hydrogencarbonate; sodium t-butanolate; bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; dimethyl sulfoxide; isopropyl alcohol; acetonitrile;

Reference yield:

6-bromo chroman-4-ol (18385-77-8) → 4-fluoro-N-[(3R,4S)-3-hydroxy-6-piperazin-1-yl-chroman-4-yl]benzamide hydrochloride (1373215-42-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / toluene / 3.83 h / 50 °C / Reflux; Industry scale

2.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C

3.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C

4.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C

4.2: 50 °C

5.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale

6.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere

6.2: pH 2.3

6.3: 1 h / 40 °C

With ammonium hydroxide; N-Bromosuccinimide; D-(+)-camphoric acid; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium t-butanolate; bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; dimethyl sulfoxide; isopropyl alcohol; toluene; acetonitrile;

upstream raw materials:

6-bromo-2H-benzopyran

6-bromo chroman-4-ol

6-bromochroman-4-one

(3R,4S)-4-amino-6-bromochroman-3-ol

Downstream raw materials:

4-fluoro-N-((3R,4S)-3-hydroxy-6-(4-(oxetan-3-yl)piperazin-1-yl)chroman-4-yl)benzamide

(3R,4S)-4-(4-fluorobenzamido)-6-(4-(oxetan-3-yl)piperazin-1-yl)chroman-3-yl methylcarbamate