Water → Ramelteon

HRID 420903Notes

Reaction equation

HRID 420903 reaction equation
Cl.[CH2:2]1[CH2:6][O:5][C:4]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][C@@H:12]([CH2:14][CH2:15][NH2:16])[C:13]=3[C:3]1=2.O.[OH-].[Na+].[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>O1CCCC1>[CH2:2]1[CH2:6][O:5][C:4]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][C@@H:12]([CH2:14][CH2:15][NH:16][C:20](=[O:23])[CH2:21][CH3:22])[C:13]=3[C:3]1=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 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 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrochloride (74 kg, 309 mol) in tetrahydrofuran (185 L) and city water (259 L) were added 30% aqueous solution of sodium hydroxide (70 L) and propionyl chloride (32.8 kg), and stirred at room temperature for 1 hr. To the reaction solution was added city water (592 L), and cooled. The precipitated crystals were collected by filtration, and dried under reduced pressure to give title compound (78.0 kg, yield 97.4%).

Workup

  1. temperaturecooled
  2. filtrationThe precipitated crystals were collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-c0f6ab72f3bf4befa80709e8fa918535
Source dataset
uspto-grants-2012_01
Patent number
US08097737B2

Reaction notes

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