Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Chloroacetyl chloride | HCID 6577 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5,8-Difluoro-1,2,3,4-Tetrahydroisoquinoline Hydrochloride | HCID 45074007 | — |
| Product | HCID 66939863 | HCID 66939863 | — |
Reaction Steps
To a stirred suspension of 5,8-di-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.69 g, 3.36 mmol) in dichloromethane (20 ml) at 0° C. under nitrogen, diisopropylethylamine (1.40 ml, 8.05 mmol) followed by chloroacetyl chloride (0.32 ml, 4.03 mmol) were added. The mixture was stirred at 0° C. for 2 hr. After being quenched with saturated sodium carbonate solution, water and dichloromethane were added. Layers were separated and the separated aqueous layer was extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered and solvents were removed in vacuum. Column purification [Hexanes-Ethyl acetate, 4:1 (v/v)] gave chloride 1AC (619 mg, 75%) as colourless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546404B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-5735e197b6a5423aaaaf6a411e62d7bf |
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| Source note | uspto-grants-2013_10 |
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