Water → HCID 21471860, compound

HRID 2294843Notes

Reaction equation

HRID 2294843 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-95c0a80c49164f278985644451aa5c2f
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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