Water → HCID 21285456, compound

HRID 1731576Notes

Reaction equation

HRID 1731576 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=O)[CH:13]([OH:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][NH:11][CH2:12][CH:13]([OH:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20227987HCID 20227987, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21285456HCID 21285456, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[2-(4-methoxyphenyl)ethyl]-2-hydroxy-1-oxo-2-(3-chlorophenyl)ethanamine (2.8 g) in dry tetrahydrofuran (20 ml) was added slowly to a refluxing suspension of lithium aluminium hydride (1.36 g) in tetrahydrofuran (30 ml) at reflux and then heated under reflux for 24 hours. After careful addition of water (1.4 ml), aqueous sodium hydroxide (10%; 1.4 ml) and water (2.8 ml), filtration and evaporation of the filtrate gave the crude product. Recrystallisation from ethyl acetate-hexane gave N-[2-(4-methoxyphenyl)-ethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine, mp 101°-3° C.

Workup

  1. temperatureat reflux
  2. temperatureheated
  3. temperatureunder reflux for 24 hours
  4. customgave the crude product
  5. customRecrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-78cbe1f5a0654af39f72215d7af262d4
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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