Aluminium lithium hydride → HCID 21859613, compound

HRID 1292907Notes

Reaction equation

HRID 1292907 reaction equation
[N:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][CH2:4]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:3]1([NH2:1])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21859610313667-22-0

Product 1

HCID 21859613HCID 21859613, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-nitroso-2,3,4,5-tetrahydro-1H-1-benzazepine (2.60 g, 14.7 mmol) in THF (40 mL) was added dropwise under N2 to a suspension of LAH (0.56 g, 14.7 mmol) in THF (10 mL) cooled with an ice-bath such that the temperature did not rise above 15° C. The mixture was stirred at room temperature for 1 h, quenched with saturated Rochelle's salt solution (15 mL) and extracted with ether (3×20 mL). The organic layer was dried (Na2SO4), concentrated in vacuo and flash column chromatography (EtOAc:hexane/1:4) gave 2,3,4,5-tetrahydro-1H-1-benzazepin-amine (1.63 g, 68%) as a light yellow solid. 1H NMR (CDCl3, 300 MHz) δ 1.50-1.72 (m, 2H), 1.78-1.92 (m, 2H), 2.70-2.82 (m, 2H), 3.180-3.22 (m, 2H), 3.78 (br, 2H), 6.91 (td, J=7.3, 1.5 Hz, 1H), 7.10 (dd, J=1.1, 7.4 Hz, 1H), 7.21 (td, J=8.0, 1.4 Hz, 1H), 7.28 (dd, J=1.4, 8.0 Hz, 1H) ppm.

Workup

  1. temperaturecooled with an ice-bath such that the temperature
  2. customdid not rise above 15° C
  3. customquenched with saturated Rochelle's salt solution (15 mL)
  4. extractionextracted with ether (3×20 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo and flash column chromatography (EtOAc:hexane/1:4)

Sources & evidence

ORD record
ord-7c14d9d90a074309ab683dc4d2d9f525
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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