Thionyl Chloride → HCID 20523673, compound

HRID 1703187Notes

Reaction equation

[CH:1]1([N:4]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]2[CH2:13]O)[CH2:3][CH2:2]1.S(Cl)([Cl:17])=O>>[CH:1]1([N:4]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]2[CH2:13][Cl:17])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 12953765HCID 12953765, compound

Product 1

HCID 20523673HCID 20523673, compound

Procedure

2-Cyclopropyl-1-hydroxymethylisoindoline (3.8 g) was stirred with thionyl chloride (35 ml) for 3 hr. Thionyl chloride was evaporated to give crude 2-cyclopropyl-1-chloromethylisoindoline (as an oil) which was dissolved in chloroform (50 ml) and treated with diethylamine (15 ml). The reaction mixture was left for 12 hr, evaporated to dryness and the residue was partitioned between aqueous sodium hydroxide and ether. The ether layer was washed (water), evaporated to dryness in vacuo, and the residue was redissolved in ether and extracted with aqueous hydrochloric acid. The acidic extract was evaporated to dryness and the residue was recrystallised from iso-propanol/ethyl acetate to give 2-cyclopropyl-1-diethylaminomethylisoindoline dihydrochloride, (0.35 g, m.p. 150°).

Workup

customThionyl chloride was evaporated

Sources & evidence

ORD record: ord-bc82bd2872624266b856bee6b23da34f
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04351842

Reaction notes

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