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Cas Database |
| Name |
Ramelteon |
EINECS | 200-835-2 |
| CAS No. | 196597-26-9 | Density | 1.119 g/cm3 |
| PSA | 38.33000 | LogP | 2.95850 |
| Solubility | N/A | Melting Point |
113-115 °C |
| Formula | C16H21NO2 | Boiling Point | 455.3 °C at 760 mmHg |
| Molecular Weight | 259.348 | Flash Point | 229.2 °C |
| Transport Information | N/A | Appearance | crystalline solid |
| Safety | 16-36/37 | Risk Codes | 11-20/21/22-36 |
| Molecular Structure |
|
Hazard Symbols | F,Xn |
| Synonyms |
Propanamide, N-(2-((8S)-1,6,7,8-tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)-;TAK-375;Rozerem;(S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide;(S)-N-[2-(1,6,7,8-Tetrahydro-2H-indeno-[5,4-b]furan-8-yl)ethyl]propionamide(196597-26-9); |
Article Data | 30 |
Ramelteon Synthetic route
- 79-03-8
propionyl chloride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| With sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; | 97.4% |
| Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride With sodium hydroxide In tetrahydrofuran; water at 15℃; Stage #2: propionyl chloride In tetrahydrofuran; water at 20℃; | 96% |
| With sodium hydroxide In tetrahydrofuran; water | 92% |
- 79-03-8
propionyl chloride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane at 0 - 20℃; | 90% |
| With sodium hydroxide In tetrahydrofuran at 20℃; for 2h; | |
| With triethylamine In dichloromethane at 20℃; for 2h; | n/a |
- 124-63-0
methanesulfonyl chloride
- 196597-88-3
(S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| Stage #1: methanesulfonyl chloride; (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide With pyridine at -10 - -5℃; for 0.833333h; Stage #2: With triethylamine In ethyl acetate Heating; Further stages.; | 86% |
| With hydrogenchloride; sodium hydrogencarbonate; triethylamine In pyridine; water; ethyl acetate |
- 196597-88-3
(S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| Stage #1: (S)-N-[2-(6-hydroxy-7-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl)ethyl]propionamide With methanesulfonyl chloride In pyridine at -10 - -5℃; for 0.833333h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate at -10 - 20℃; for 0.5h; Stage #3: With triethylamine for 0.666667h; Heating / reflux; | 86% |
- 79-03-8
propionyl chloride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid With water; sodium hydroxide In tetrahydrofuran at -10℃; Stage #2: propionyl chloride In tetrahydrofuran at -10 - 20℃; for 2h; | 85% |
| Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid With sodium hydroxide In dichloromethane; water Stage #2: propionyl chloride In tetrahydrofuran; water at 20℃; Cooling with ice; |
- 1185516-79-3
(S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile
- 123-62-6
propionic acid anhydride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| Stage #1: (S)-2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetonitrile; propionic acid anhydride With hydrogen; Raney-Ni In tetrahydrofuran at 80℃; under 3000.3 Torr; Stage #2: With sodium hydroxide In tetrahydrofuran; toluene for 0.5h; | 81% |
| With hydrogen; platinum on carbon In tetrahydrofuran at 65℃; under 7500.75 - 9000.9 Torr; Product distribution / selectivity; |
- 79-03-8
propionyl chloride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| With sodium carbonate In dichloromethane; water at -5 - 10℃; | 80% |
- 123-62-6
propionic acid anhydride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 10 - 60℃; pH=6.0 - 6.5; | 73% |
| Stage #1: (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride With sodium hydroxide In tetrahydrofuran; water Stage #2: propionic acid anhydride In tetrahydrofuran; water at 20 - 25℃; |
- 123-62-6
propionic acid anhydride
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane at 20℃; for 1h; optical yield given as %ee; | 62% |
- 79-05-0
Propionamid
- 196597-26-9
ramelteon
| Conditions | Yield |
|---|---|
| With triethylsilane; trifluoroacetic acid In toluene at 80℃; for 24h; | 54% |
Ramelteon Chemical Properties
Product Name: Ramelteon (CAS NO.196597-26-9)
Molecular Formula: C16H21NO2
Molecular Weight: 259.34g/mol
Mol File: 196597-26-9.mol
Melting Point: 113-1150C
Boiling point: 455.3 °C at 760 mmHg
Flash Point: 229.2 °C
Density: 1.119 g/cm3
Surface Tension: 45.2 dyne/cm
Enthalpy of Vaporization: 71.51 kJ/mol
Vapour Pressure: 1.77E-08 mmHg at 25°C
XLogP3-AA: 2.7
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of Ramelteon (CAS NO.196597-26-9):
IUPAC Name: N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide
Canonical SMILES: CCC(=O)NCCC1CCC2=C1C3=C(C=C2)OCC3
Isomeric SMILES: CCC(=O)NCC[C@@H]1CCC2=C1C3=C(C=C2)OCC3
InChI: InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1
InChIKey: YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Product Categories: Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals
Ramelteon Specification
Ramelteon , its CAS NO. is 196597-26-9, the synonyms are (-)-N-(2-(((8S)-1,6,7,8-Tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)propanamide ; (S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide ; Propanamide, N-(2-((8S)-1,6,7,8-tetrahydro-2H-indeno(5,4-b)furan-8-yl)ethyl)- ; Rozerem ; TAK-375 ; UNII-901AS54I69 .
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