Water → Ramelteon

HRID 1636613Notes

Reaction equation

HRID 1636613 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-3130191e2e114f7893be371903e28797
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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