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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 912744Generated: October 27, 2026

Hydrochloric Acid → 3-[(1-Naphthyloxy)methyl]pyrrolidine

https://huagongshe.com/reaction/912744

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant1,1-Dimethylethyl 3-[(1-naphthalenyloxy)methyl]-1-pyrrolidinecarboxylateHCID 67416450—
Solvent1,4-DioxaneHCID 31275—
Product3-[(1-Naphthyloxy)methyl]pyrrolidineHCID 4507557772.2%

Reaction Steps

A solution of 0.42 g (1.28 mmol) of 1,1-dimethylethyl 3-[(1-naphthalenyloxy)methyl]-1-pyrrolidinecarboxylate, prepared in Step 12.1., in 10 ml of 1,4-dioxane and 6 ml of a 2N solution of aqueous hydrochloric acid is stirred for 6 hours. It is evaporated to dryness and then coevaporation is carried out twice with toluene. The solid residue is washed with diethyl ether. The solid is taken up in dichloromethane and concentrated ammonia solution is added until a basic pH is obtained. The system is filtered on a Whatman PTFE cartridge and the organic phase is concentrated, to give 0.21 g of oily product, which is used as it is in the following step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08026258B2
Source datasetuspto-grants-2011_09
ORD IDord-5371b4a746d3447b9194244ba14611c6
Source noteuspto-grants-2011_09