Water → HCID 19040650, compound

HRID 1683764Notes

Reaction equation

HRID 1683764 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18][C:12]=2[C:11]([O:20][CH2:21][C:22](OCC)=O)=[CH:10][CH:9]=1.[OH2:27].[OH-].[Na+]>C(OCC)C>[Cl:7][C:8]1[C:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18][C:12]=2[C:11]([O:20][CH:21]([OH:27])[CH3:22])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53861417HCID 53861417, compound

Product 1

HCID 19040650HCID 19040650, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (1.53 g, 40 mmol) in ethyl ether (80 ml) was stirred, heated to reflux and treated with a solution of ethyl [(9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-6-yl)oxy]acetate (4.0 g, 13.5 mmol) in ethyl ether (60 ml). The mixture was stirred at reflux for 3.5 hours, cooled, and carefully treated with water (1.5 ml), 10% sodium hydroxide (4.5 ml) and water (1.5 ml). The mixture was filtered and the filtrate dried with magnesium sulfate and concentrated to give 3,2 g (91%) of [(9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-6-yl)oxy]ethanol.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureat reflux for 3.5 hours
  4. temperaturecooled
  5. filtrationThe mixture was filtered
  6. dry with materialthe filtrate dried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c879bdc1173d4867ae42f2a661000fbe
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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