Benzylamine → 6-Benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

HRID 253989Notes

Reaction equation

HRID 253989 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[O:9][CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14]OS(C)(=O)=O)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCOCC1>[CH2:26]([N:33]1[CH2:6][CH2:7][C:8]2[O:9][CH:10]=[CH:11][C:12]=2[CH2:13][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 866023872,3-Di(2-methanesulfonyloxyethyl)furan

Product 1

HCID 196001856-Benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
102 °C

Procedure

A solution of 2,3-di(2-methanesulfonyloxyethyl)furan (114 mmol) in dioxane (168 mL) is treated with potassium carbonate (337 mmol) and benzyl amine (70.1 mmol) and heated to 102° C. for 18 hours. The reaction is cooled, the precipitate removed by filtration, and the mother liquor concentrated to give a crude oil which is purified by silica chromatography (EtOAc/hexanes eluant) to provide 6-benzyl-5,6,7,8-tetrahydro-4H-furo[3,2-d]azepine.

Workup

  1. temperatureThe reaction is cooled
  2. customthe precipitate removed by filtration
  3. concentrationthe mother liquor concentrated
  4. customto give a crude oil which
  5. customis purified by silica chromatography (EtOAc/hexanes eluant)

Sources & evidence

ORD record
ord-3f0a9d1a984b4a5cb57e699822504956
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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