Nitrogen → 2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 1375347Notes

Reaction equation

HRID 1375347 reaction equation
N#N.[NH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][C:4]1=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 947NitrogenHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under anhydrous conditions and N2 atmosphere, 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (100 mg) in THF (5 ml) was treated with LiAlH4 (0.65 ml @ 1.0M in THF). The resulting solution was heated at reflux for 1 hr. The reaction was quenched by addition to a small amount of ice. The resulting mixture was diluted with a large excess of CH3CN (˜50:1) and filtered. The filtrate was concentrated in vacuo to give 84 mg of the titled product. 1H NMR (300 MHz, CDCl3) 1.69 (m, 2H), 1.86 (m, 2H), 2.82 (m, 2H), 3.10 (m, 2H), 3.6 (bs, 1H), 6.80 (d, J=7.8 Hz, 1H), 6.88 (t, J=7.3 Hz, 1H), 7.09 (dt, J=7.6 Hz, J=1.4 Hz, 1H), 7.15 (d, J=7.4 Hz, 1H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 1 hr
  3. customThe reaction was quenched by addition to a small amount of ice
  4. additionThe resulting mixture was diluted with a large excess of CH3CN (˜50:1)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-81beef8b3109427385e992b58068703c
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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