Dimethylamine, hydrochloride → HCID 18357454, compound

HRID 1422135Notes

Reaction equation

HRID 1422135 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)=[N:2]1.[ClH:18].[CH3:19][NH:20][CH3:21].[BH4-].[Na+]>CO.C(OCC)(=O)C>[ClH:18].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH2:12][N:20]([CH3:21])[CH3:19])=[N:2]1

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 15550297HCID 15550297, compound

Product 1

HCID 18357454HCID 18357454, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In one portion, a total of 2.0 g of 2-(1,2-benzisoxazol-3-yl)-benzaldehyde was added to a solution of 8.0 g of dimethylamine hydrochloride in 70 ml of methanol. The reaction mixture was stirred at room temperature for 16 h, after which 2.0 g of sodium borohydride were added. After stirring at room temperature for another 24 h, the solids were filtered off, and the residue was washed with dichloromethane. The combined filtrate was dried over magnesium sulphate and evaporated to dryness under reduced pressure. The resulting solid was purified by chromatography on silica gel, eluting with ethyl acetate, affording 0.89 g. This solid was dissolved in ethyl acetate, and triturated with a solution of hydrogen chloride in methanol. This solution was evaporated to dryness under reduced pressure and the residue was crystallised from ethanol/diethyl ether/hexane, yielding 0.54 g of pure 2-(1,2-benzisoxazol-3-yl)-N, N-dimethyl-benzenemethanamine hydrochloride, melting at 190° C.

Workup

  1. stirringAfter stirring at room temperature for another 24 h
  2. filtrationthe solids were filtered off
  3. washthe residue was washed with dichloromethane
  4. dry with materialThe combined filtrate was dried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customThe resulting solid was purified by chromatography on silica gel
  7. washeluting with ethyl acetate
  8. customaffording 0.89 g
  9. customtriturated with a solution of hydrogen chloride in methanol
  10. customThis solution was evaporated to dryness under reduced pressure
  11. customthe residue was crystallised from ethanol/diethyl ether/hexane

Sources & evidence

ORD record
ord-73c5ec13c2904092af357f94d45a949e
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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