Water → Ramelteon

HRID 324640Notes

Reaction equation

HRID 324640 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].Cl.[CH2:7]1[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]3[CH2:15][CH2:16][C@@H:17]([CH2:19][CH2:20][NH2:21])[C:18]=3[C:8]1=2.C(N(CC)CC)C.O>CN(C)C=O>[CH2:7]1[CH2:11][O:10][C:9]2[CH:12]=[CH:13][C:14]3[CH2:15][CH2:16][C@@H:17]([CH2:19][CH2:20][NH:21][C:1](=[O:4])[CH2:2][CH3:3])[C:18]=3[C:8]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 453587792-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethanamine hydrochloride (1:1)

Product 1

HCID 208902RamelteonYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propionyl chloride (2.57 g, 27.8 mmol.) was gradually added dropwise, under ice-cooling, to a solution of (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl) ethylamine hydrochloride (5.55 g, 23.1 mmol.) and triethylamine (4.7 g, 46.3 mmol.) in N,N-dimethylformamide (100 ml). The mixture was stirred for one hour at room temperature, which was then poured into water, followed by extracting the organic matter with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate:methanol=98:2) to afford the title compound (yield 5.25 g, 88%).

Workup

  1. extractionby extracting the organic matter with ethyl acetate
  2. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by means of silica gel column chromatography (ethyl acetate:methanol=98:2)

Sources & evidence

ORD record
ord-6e14916021b14c3b8715cfe7dd2daddf
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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