Hydrochloric Acid → 62922-45-6

HRID 1156220Notes

Reaction equation

[CH2:1]([NH2:7])[CH:2]1O[CH2:5][CH2:4][CH2:3]1.[ClH:8].S(Cl)([Cl:11])=O>>[ClH:11].[Cl:8][CH:2]([CH2:3][CH2:4][CH2:5][Cl:11])[CH2:1][NH2:7]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 24386Thionyl Chloride

HCID 253298Tetrahydrofurfurylamine

Product 1

HCID 273757262922-45-6

Procedure

An N-alkenyl-2-aminomethyl-pyrrolidine is prepared by firstly reacting tetrahydrofurfurylamine with gaseous hydrochloric acid and thionyl chloride to produce 2,5 dichloropentylamine hydrochloride. This is acetylized, possibly by acetyl chloride in dichloroethane in the presence of triethylamine, into N-acetyl-2,5-dichloropentylamine which is condensed with an alkenylamine into an N-alkenyl-2-acetylaminomethyl pyrrolidine from which the acetyl group is separated, for example by boiling with concentrated hydrochloric acid.

Sources & evidence

ORD record: ord-ba9f83f505294d32bd736dad2b39deee
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04335045

Reaction notes

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