Chloro-APB hydrobromide

Base Information

• Chemical Name: Chloro-APB hydrobromide
• CAS No.: 74115-01-8
• Molecular Formula: C19H20 Cl N O2 . Br H
• Molecular Weight: 410.738
• DSSTox Substance ID: DTXSID401017951
• Wikipedia: SKF-82,958
• Pharos Ligand ID: XUHQSTX8H2ZK
• ChEMBL ID: CHEMBL544115
• Mol file: 74115-01-8.mol

Synonyms:6-chloro-7,8-dihydroxy-3-allyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine;Cl-APB;SK and F 82958;SK and F-82958;SKF 82958;SKF-82958

Chemical Property of Chloro-APB hydrobromide

Chemical Property:

• Melting Point: 203-204 °C(Solv: isopropanol (67-63-0); ethyl ether (60-29-7))
• PSA: 43.70000
• LogP: 4.82320
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 409.04442
• Heavy Atom Count: 24
• Complexity: 399

Purity/Quality:

99% ^*data from raw suppliers

SKF82958Hydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1CCC2=C(C(=C(C=C2C(C1)C3=CC=CC=C3)O)O)Cl.Br
• Uses: SKF 82958 Hydrobromide is a dopamine (D1) agonist. Also, it augments GABAB inhibitory post-synaptic potentials (ipsp) in ventral tegmental area in brain slices.

Technology Process of Chloro-APB hydrobromide

There total 9 articles about Chloro-APB hydrobromide 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: 45.0%

3-allyl-6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (74115-02-9) → 3-allyl-6-chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (74115-01-8)

Guidance literature:

With boron tribromide; In hexane; dichloromethane; 1.) -70 deg C, 1 h, 2.) RT, 2 h;

DOI:10.1021/jm00116a004

Reference yield:

1H-benzo[b]azepine (264-54-0) + 6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (67287-38-1) + allyl bromide (106-95-6) → 3-allyl-6-chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (74115-01-8)

Guidance literature:

With boron tribromide; potassium carbonate; In N-methyl-acetamide; methanol; dichloromethane; chloroform; ethyl acetate; isopropyl alcohol;

Reference yield:

N-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine (20011-97-6) → 3-allyl-6-chloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (74115-01-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / trifluoroacetic acid, H₂SO₄ / 3 h / Heating

2: 69 percent / glacial acetic acid, bromine / 2 h / Ambient temperature

3: 85 percent / formic acid / 4 h / Heating

4: 1.) n-BuLi, 2.) hexachloroethane / 1.) Et₂O, THF, -70 deg C, 10 min, 2.) Et₂O, THF, -70 deg C, 5 min

5: 3.1 g / benzene / 3 h / 60 °C

6: aq. HCl / acetic acid / 100 °C

7: 50 percent / K₂CO₃ / dimethylformamide; H₂O; diethyl ether / Ambient temperature

8: 45 percent / boron tribromide / CH₂Cl₂; hexane / 1.) -70 deg C, 1 h, 2.) RT, 2 h

With hydrogenchloride; n-butyllithium; formic acid; hexachloroethane; sulfuric acid; bromine; boron tribromide; potassium carbonate; acetic acid; trifluoroacetic acid; In diethyl ether; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00116a004

upstream raw materials:

3-allyl-6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

N-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine

7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Downstream raw materials:

Acetic acid 8-acetoxy-3-allyl-9-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl ester

Refernces

• 1、 Pfeiffer,Wilson,Weinstock,Kuo,Chambers,Holden,Hahn,Wardell Jr.,Tobia,Setler,Sarau. "Dopaminergic activity of substituted 6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines". . p. 352 - 358. Retrieved 2007/10/02.