Water → HCID 13037478, compound

HRID 1156479Notes

Reaction equation

HRID 1156479 reaction equation
[CH3:1][CH:2]1[O:7][C:6]([C:15]#[N:16])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][CH2:4][O:3]1.COCCO[AlH2-]OCCOC.[Na+].O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH3:1][CH:2]1[O:7][C:6]([CH2:15][NH2:16])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][CH2:4][O:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 13037477HCID 13037477, compoundHCID 16684438Red-Al

Product 1

HCID 13037478HCID 13037478, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

Thirty-two g (0.135 mole) of 2-methyl-4-(cyano)-4-(2-chlorophenyl)-1,3-dioxane was dissolved in 100 ml of toluene. To this solution was added 60 g (0.21 mole) of red-al in benzene (Aldrich Chemical Company). The reaction exothermed to 40° C. The reaction was allowed to stir 1 hour at room temperature and was then heated at 90° C. for 5 hours. The reaction was stirred overnight at room temperature. The reaction was quenced by the cautious addition of H2O. One hundred ml of saturated NH4Cl was added and the slurry was filtered. The layers were separated and the organic layer was dried and stripped to yield 25.6 g of 2-methyl-4-(aminomethyl)-4-(2-chlorophenyl)-1,3-dioxane. Structure as confirmed by infrared, nuclear magnetic resonance and mass spectroscopy.

Workup

  1. customexothermed to 40° C
  2. temperaturewas then heated at 90° C. for 5 hours
  3. stirringThe reaction was stirred overnight at room temperature
  4. filtrationthe slurry was filtered
  5. customThe layers were separated
  6. customthe organic layer was dried

Sources & evidence

ORD record
ord-0e764adc7861447d956fb29e2ce860ce
Source dataset
uspto-grants-1982_06
Patent number
US04336058

Reaction notes

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