Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | Ammonium Carbonate | HCID 517111 | — |
| Reactant | HCID 13677787 | HCID 13677787 | — |
| Product | HCID 67922902 | HCID 67922902 | 26.7% |
Reaction Steps
To a stirred suspension of 3.97 parts of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-(4-oxopentyl)-4-piperidinyl]benzamide in 19.2 parts of ethanol was added first a solution of 0.72 parts of potassium cyanide in 12 parts of water and then 2.88 parts of ammonium carbonate. The whole was stirred overnight at about 55° C. After cooling, the reaction mixture was poured into water. Ethanol was evaporated whereupon a precipitate was formed. It was filtered off, washed with water and boiled twice in acetonitrile. The product was filtered off and crystallized from 4-methyl-2-pentanone, yielding 1.25 parts (26.7%) of cis-4-amino-5-chloro-2-methoxy-N-[3-methoxy-1-[3-(4-methyl-2,5-dioxo-4-imidazolidinyl)propyl]-4-piperidinyl]benzamide; mp. 235.8° C. (compound 90).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04975439 |
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| Source dataset | uspto-grants-1990_12 |
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| ORD ID | ord-eb808ddc48f042df9c385533d19b1395 |
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| Source note | uspto-grants-1990_12 |
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