Water → Ramelteon

HRID 1699749Notes

Reaction equation

HRID 1699749 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.[OH-].[Na+].[C:19](Cl)(=[O:22])[CH2:20][CH3:21].O>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:19](=[O:22])[CH2:20][CH3:21])[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 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrochloride (100.0 g, 417 mmol) in tetrahydrofuran (250 mL) at 15° C. was added dropwise a 7.1% aqueous solution of sodium hydroxide (538 mL). Propionyl chloride (44.4 g, 480 mmol) was added dropwise to the reaction mixture. Stirring was continued at room temperature for 30 min. Water (800 mL) was added and crystals precipitated were collected by filtration followed by recrystallization from ethanol:water=1:2 to obtain 99.5 g (yield: 92%) of the title compound.

Workup

  1. customcrystals precipitated
  2. filtrationwere collected by filtration
  3. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-b98eedd09ee04b88b0b38d00e22adcb9
Source dataset
uspto-grants-2002_02
Patent number
US06348485B1

Reaction notes

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