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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1493377Generated: October 26, 2026

Dimethylformamide → Butenafine Hydrochloride

https://huagongshe.com/reaction/1493377

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium CarbonateHCID 10340—
ReactantN-Methyl-N-naphthylmethylamineHCID 84474—
ReactantBenzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 88198—
SolventWaterHCID 962—
ProductButenafine HydrochlorideHCID 443867—

Reaction Conditions

Temperature50 °C

Reaction Steps

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. Melting point: 210° to 212° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05021458
Source datasetuspto-grants-1991_06
ORD IDord-b6a5203f5a8047c19c410a339c0e4bbf
Source noteuspto-grants-1991_06