Thionyl Chloride → Benzeneethanamine, 4-chloro-N-(2-chloropropyl)-, hydrochloride (1:1)

HRID 71059Notes

Reaction equation

[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH2:7][NH:8][CH2:9][CH:10](O)[CH3:11])=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[ClH:1].[Cl:17][CH:10]([CH3:11])[CH2:9][NH:8][CH2:7][CH2:6][C:5]1[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 115647501-((4-Chlorophenethyl)amino)propan-2-ol

Product 1

HCID 44222956Benzeneethanamine, 4-chloro-N-(2-chloropropyl)-, hydrochloride (1:1)

Procedure

In some embodiments, after reacting 1-(4-chlorophenethylamino)propan-2-ol with thionyl chloride, produces 2-chloro-N-(4-chlorophenethyl)propan-1-amine hydrochloride with a purity of about 95% or greater as determined by HPLC. In some embodiments, after reacting 1-(4-chlorophenethylamino)propan-2-ol with thionyl chloride, the 2-chloro-N-(4-chlorophenethyl)propan-1-amine hydrochloride with a purity of about 98% or greater as determined by HPLC. In some embodiments, “HPLC” refers to Reversed-Phase High Performance Liquid Chromatography. In some embodiments, “HPLC” refers to Normal-Phase High Performance Liquid Chromatography.

Sources & evidence

ORD record: ord-75a4634ab12f4e5e94128d63d8b7edb5
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822727B2

Reaction notes

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