Sodium Hydroxide → HCID 23043611, compound

HRID 2165093Notes

Reaction equation

HRID 2165093 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:19]=2)=[CH:12][CH:11]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[OH-].[Na+]>C1COCC1.O>[CH3:7][NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:19]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23043601HCID 23043601, compoundHCID 68718528lithium aluminium hydride THF

Product 1

HCID 23043611HCID 23043611, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (0.25 g, 6.5 mmole) is added to dry THF (20 ml) under an inert atmosphere, then cooled to ~4° C. (ice/water bath). N-formyl-4-[2-(3,4-dibenzyloxyphenyl)ethyl]benzeneamine (2.9 g, 6.5 mmole) is dissolved in dry THF (20 ml) and added via cannula dropwise to the LAH/THF suspension. The reaction is stirred for 20 hours at ambient temperature under an inert atmosphere. Water (0.25 ml) followed by 15% NaOH (0.25 ml) and finally water (0.75 ml) is added to the reaction mixture. The mixture is filtered, diluted with 0.5 volume of ether, and the organics are washed with brine and then dried (Na2SO4). Concentration affords 1.9 g (70% g) of N-methyl-4-[2-(3,4-dibenzyloxyphenyl)ethyl]benzeneamine, mp 61°-65° C., of sufficient purity for further use.

Workup

  1. additionis added to the reaction mixture
  2. filtrationThe mixture is filtered
  3. additiondiluted with 0.5 volume of ether
  4. washthe organics are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration

Sources & evidence

ORD record
ord-833f0b24d62e4977bc89a1b2a43b3758
Source dataset
uspto-grants-1990_07
Patent number
US04939133

Reaction notes

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