Water → HCID 21471860, compound

HRID 1734067Notes

Reaction equation

HRID 1734067 reaction equation
[S:1]1[C:5]2[C:6](=O)[NH:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.[BH4-].[Na+].O>O1CCCC1>[S:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21471822HCID 21471822, compound

Product 1

HCID 21471860HCID 21471860, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6.7 g of 4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one and 4.5 g of sodium borohydride in 70 ml of tetrahydrofuran was added boron trifluoride-ether complex dropwise under ice-cooling and the mixture was refluxed under heating for an hour. The mixture was poured into water, washed with chloroform, made alkaline with 10% potassium hydroxide solution and extracted with chloroform. The extract was washed with water, dried and concentrated to give 4.1 g of 5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine as an oil.

Workup

  1. additionwas added boron trifluoride-ether complex dropwise under ice-
  2. temperaturecooling
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for an hour
  5. washwashed with chloroform
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-881cec23a4264c1badec9b594daa163d
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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