Formaldehyde → HCID 21162632, compound

HRID 893993Notes

Reaction equation

HRID 893993 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([C:20]([CH3:22])=[O:21])=[CH:16][CH:15]=1.[CH2:24]=O.[OH-].[Na+]>CO.Cl.O>[CH3:1][N:2]([CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:24][CH2:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:23])=[CH:15][CH:16]=1)=[O:21]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 8500p-METHYLACETOPHENONEHCID 14798Sodium HydroxideHCID 84474N-Methyl-N-naphthylmethylamine

Product 1

HCID 21162632HCID 21162632, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

17.1 g of methyl-(1-naphthylmethyl)amine are dissolved in 200 ml of methanol and 10 ml of concentrated hydrochloric acid, 13.4 g of 4-tolylmethylketone and 100 ml of 35% formaldehyde solution are sequentially added. The mixture is refluxed for 11/2 hours, with stirring, cooled, diluted with 1 liter of water, made alkaline with 30% sodium hydroxide solution and exhaustively extracted with chloroform. The organic extract is dried and evaporated to dryness and the oily residue is dissolved in petroleum ether and allowed to crystallise in the cold, to obtain the heading compound, m.p. 92°-95°.

Workup

  1. temperatureThe mixture is refluxed for 11/2 hours
  2. temperaturecooled
  3. extractionexhaustively extracted with chloroform
  4. extractionThe organic extract
  5. customis dried
  6. customevaporated to dryness
  7. dissolutionthe oily residue is dissolved in petroleum ether
  8. customto crystallise in the cold,
  9. customto obtain the heading compound, m.p. 92°-95°

Sources & evidence

ORD record
ord-547fc8fe79b24eb099dba11f93e3baeb
Source dataset
uspto-grants-1981_08
Patent number
US04282251

Reaction notes

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