Dimethylformamide → Butenafine Hydrochloride

HRID 1589877

Reaction equation

HRID 1589877 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]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][Cl:23])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[ClH:23].[C:14]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:2]([CH2:3][C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[CH:6][CH:5]=2)[CH3:1])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 84474N-Methyl-N-naphthylmethylamineHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-

Product 1

HCID 443867Butenafine Hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3.43 g of N-methyl-naphthylmethylamine, 3.65 g of 4-tert-butylbenzyl chloride, 2.33 g of anhydrous sodium carbonate and 20 ml of dimethyl formamide was stirred at 50° C. for 16 hours. The reaction mixture was poured into water and extracted with benzene, and the benzene solution was washed with water. After distilling away benzene, 3 ml of concentrated hydrochloric acid was added at cooling. An excess of hydrochloric acid was removed under reduced pressure and a suitable amount of acetone was added. White crystal (5.9 g) was precipitated and was filtered. N-(4-tert-butylbenzyl)-N-methyl-1-naphthylmethylamine hydrochloride of white plate crystal (Compound of Example 1) was obtained by recrystallization from acetone/ethanol.

Workup

  1. extractionextracted with benzene
  2. washthe benzene solution was washed with water
  3. distillationAfter distilling away benzene, 3 ml of concentrated hydrochloric acid
  4. additionwas added
  5. temperatureat cooling
  6. customAn excess of hydrochloric acid was removed under reduced pressure
  7. additiona suitable amount of acetone was added
  8. customWhite crystal (5.9 g) was precipitated
  9. filtrationwas filtered

Sources & evidence

ORD record
ord-cb29cb6339f54731b56e22896d06c4fe
Source dataset
uspto-grants-1993_04
Patent number
US05200423

Linked notes

Loading…