Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | HCID 20203546 | HCID 20203546 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 13749180 | HCID 13749180 | 77% |
Reaction Steps
A mixture of formic acid (8.5 g,) and acetic anhydride (15.2 g) was heated to 60° C. for 4 hours, then cooled to 0° C. A solution of 6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-amine (6.1 g, 26.6 mmol) in tetrahydrofuran (50 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours under exclusion of moisture. It was then poured into water (75 mL) and extracted with ether (3×100 mL). The combined organic layers were washed with 5% hydrochloric acid (50 mL), and then with saturated sodium bicarbonate (3×50 mL). The separated organic layer was dried over MgSO4, filtered, and evaporated to afford 5.25 g (77%) of the title compound as an off white solid, m.p. 181°-182.5° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04624954 |
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| Source dataset | uspto-grants-1986_11 |
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| ORD ID | ord-8636ad9933b64f7482666b3579959c86 |
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| Source note | uspto-grants-1986_11 |
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