Water → (2,3,4,5-tetrahydro-1H-1-benzazepin-2-yl)methanamine

HRID 1035309Notes

Reaction equation

HRID 1035309 reaction equation
[N+:1](/[CH:4]=[C:5]1\[NH:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][CH2:11]\1)([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][CH2:11][CH:5]1[CH2:4][NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 13842538(2z)-2-(Nitromethylene)-2,3,4,5-tetrahydro-1h-1-benzazepineHCID 21226445Aluminium lithium hydride

Product 1

HCID 13842540(2,3,4,5-tetrahydro-1H-1-benzazepin-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Example 182D (0.643 g, 3.15 mmol) in tetrahydrofuran (31.5 mL) under argon was added dropwise lithium aluminum hydride in tetrahydrofuran (9.45 mL, 18.89 mmol), and the mixture was stirred at room temperature for 30 minutes. Water was added carefully and the mixture was extracted once with dichloromethane. The organic extract was dried over Na2SO4, and the solvent was evaporated to obtain the crude title compound which was used was used without purification for the next reaction. MS (ESI+) m/z 177.3 (M+H)+.

Workup

  1. extractionthe mixture was extracted once with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bf9c9902712b468197a4d7c765d4957c
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

Loading…