Ethanol → HCID 67922902, compound

HRID 2248635Notes

Reaction equation

HRID 2248635 reaction equation
[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18](=O)[CH3:19])[CH2:11][C@H:10]2[O:21][CH3:22])=[O:7])=[C:4](OC)[CH:3]=1.[CH2:28]([OH:30])C.[C-:31]#[N:32].[K+].[C:34](=[O:37])([O-])[O-].[NH4+:38].[NH4+].[OH2:40]>>[NH2:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3([CH3:19])[C:31](=[O:40])[NH:32][C:28](=[O:30])[NH:38]3)[CH2:11][C@H:10]2[O:21][CH3:22])=[O:7])=[C:4]([O:37][CH3:34])[CH:3]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962Water2×HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 13677787HCID 13677787, compound

Product 1

HCID 67922902HCID 67922902, compoundYield 26.7%

Conditions

Temperature
55 °C

Procedure

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).

Workup

  1. temperatureAfter cooling
  2. customEthanol was evaporated whereupon a precipitate
  3. customwas formed
  4. filtrationIt was filtered off
  5. washwashed with water
  6. filtrationThe product was filtered off
  7. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-599f40af2fc0452e817fec4aea2a4a6b
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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