Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Maleic Acid | HCID 444266 | — |
| Reactant | Glycinamide hydrochloride | HCID 2723639 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 1-Acetyl-1-(3,4-dichlorophenyl)cyclobutane | HCID 13083139 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 20225042 | HCID 20225042 | — |
Reaction Steps
A mixture of 1-acetyl-1-(3,4-dichlorophenyl)cyclobutane (2.43 g), glycinamide hydrochloride (2.21 g) powdered potassium hydroxide (1.2 g) and sodium cyanoborohydride (1.5 g) in methanol (20 ml) was stirred at 0°-5° C. for 2 hours then for a total of 10 days at ambient temperature. The mixture was cooled and 5N hydrochloric acid added. The mixture was then basified, extracted into ether, washed with water, dried and evaporated to give an oil. This oil was dissolved in ether and a solution of maleic acid (1.0 g) in dry ether (100 ml) was added to give an oil which was dissolved in acetone. Ether was then added to give a white solid which was dissolved in water, basified and extracted into ether. Passing hydrogen chloride gas through the dried ethereal extract gave 2-{1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamino}acetamide hydrochloride (m.p. 240°-245° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04629727 |
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| Source dataset | uspto-grants-1986_12 |
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| ORD ID | ord-65504fee27c14af48d7d367b1a42a84d |
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| Source note | uspto-grants-1986_12 |
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