Water → 5,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

HRID 2375159Notes

Reaction equation

HRID 2375159 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[N:10]O)[CH2:7][CH2:8][CH2:9][C:2]1=2.[H-].C([Al+]CC(C)C)C(C)C.[F-].[Na+].O>ClCCl>[S:1]1[C:2]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:10][C:3]=2[CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 29898N-(4,5,6,7-tetrahydro-1-benzothiophen-4-ylidene)hydroxylamineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepineYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6,7-dihydro-5H-benzo[b]thiophen-4-one oxime (1.67 g) in dry dichloromethane (100 mL) was cooled to 0°. Following dropwise addition of diisobutylaluminum hydride (50 ml, 1M in hexanes), the mixture was stirred at 0° for three hours and then diluted with dichloromethane (50 mL). Sodium fluoride (8.4 g) was added, followed by water (2.7 mL). The reaction mixture was stirred vigorously for 30 minutes, then filtered. and concentrated to provide the title compound (0.81 g) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred vigorously for 30 minutes
  2. filtrationfiltered
  3. concentrationand concentrated

Sources & evidence

ORD record
ord-af52600af7c94afca7cd4a35251c18be
Source dataset
uspto-grants-2008_12
Patent number
US07465722B2

Reaction notes

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