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196597-26-9

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Basic Information
CAS No.: 196597-26-9
Name: Ramelteon
Article Data: 30
Molecular Structure:
Molecular Structure of 196597-26-9 (Ramelteon)
Formula: C16H21NO2
Molecular Weight: 259.348
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);
EINECS: 200-835-2
Density: 1.119 g/cm3
Melting Point: 113-115 °C
Boiling Point: 455.3 °C at 760 mmHg
Flash Point: 229.2 °C
Appearance: crystalline solid
Hazard Symbols: F,Xn
Risk Codes: 11-20/21/22-36
Safety: 16-36/37
PSA: 38.33000
LogP: 2.95850
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Conditions
ConditionsYield
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; water92%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine

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propionyl chloride

196597-26-9

ramelteon

Conditions
ConditionsYield
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
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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

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Conditions
ConditionsYield
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
ConditionsYield
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%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid

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propionyl chloride

196597-26-9

ramelteon

Conditions
ConditionsYield
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

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propionic acid anhydride

196597-26-9

ramelteon

Conditions
ConditionsYield
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;

2-[(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethanamine oxalate

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propionyl chloride

196597-26-9

ramelteon

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water at -5 - 10℃;80%

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine hydrochloride

123-62-6

propionic acid anhydride

196597-26-9

ramelteon

Conditions
ConditionsYield
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℃;

(S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)-ethylamine

123-62-6

propionic acid anhydride

196597-26-9

ramelteon

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h; optical yield given as %ee;62%

2-((S)-2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)acetaldehyde

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Propionamid

196597-26-9

ramelteon

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In toluene at 80℃; for 24h;54%
Raw Materials
123-62-6
13623-25-1
196597-86-1
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Chemistry

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

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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