Water → HCID 67928382, compound

HRID 727943Notes

Reaction equation

HRID 727943 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:9][CH2:10][CH2:11][O:12][C:13]1[CH:35]=[CH:34][C:16]([CH2:17][CH2:18][NH:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28][C:29]([O:31]CC)=[O:30])=O)=[CH:15][CH:14]=1)[CH3:8].[OH2:36].[OH-:37].[Na+]>C(OCC)C>[C:28]([OH:37])(=[O:36])[C:29]([OH:31])=[O:30].[CH2:7]([O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH2:18][NH:19][CH2:20][CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:29][CH:28]=2)[CH2:27][OH:36])=[CH:34][CH:35]=1)[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54260255HCID 54260255, compound

Product 1

HCID 67928382HCID 67928382, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 15 g of LiAlH4 in 600 ml of diethyl ether was treated while stirring with a solution of 20 g of ethyl [[[p-(2-ethoxyethoxy)phenethyl]carbamoyl]phenyl]-acetate. After stirring for 12 hours 15 ml of water and 5 ml of 10% sodium hydroxide solution were added to the mixture. The mixture was filtered through silica gel and the filtrate was evaporated. The residue was dissolved in ethanol and treated with the equivalent amount of oxalic acid dissolved in ethanol. After adding ethyl acetate there was obtained β-[[[p-(2-ethoxyethoxy)phenethyl]amino]methyl]phenethyl alcohol oxalate m.p. 145° C.

Workup

  1. additionwere added to the mixture
  2. filtrationThe mixture was filtered through silica gel
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethanol
  5. additiontreated with the equivalent amount of oxalic acid
  6. dissolutiondissolved in ethanol
  7. additionAfter adding ethyl acetate there

Sources & evidence

ORD record
ord-1cd8ca8d3c8e4b07aa5d81b3045fefb9
Source dataset
uspto-grants-1991_09
Patent number
US05045567

Reaction notes

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