Isatoic Anhydride → HCID 86758637, compound

HRID 2297519Notes

Reaction equation

HRID 2297519 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)OC2=O.[C:13]1([CH:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH2:29])[CH2:22][CH2:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O:36]1CCOC[CH2:37]1>>[C:30]1([CH:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][N:29]([C:1]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH2:6])[CH:37]=[O:36])[CH2:24][CH2:25]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 8359Isatoic AnhydrideHCID 312751,4-DioxaneHCID 137677783-(4-Benzhydryl-1-piperazinyl)-1-propanamine

Product 1

HCID 86758637HCID 86758637, compoundYield 92%

Procedure

Isatoic anhydride (1.02 g) and 1-diphenylmethyl-4-(3-aminopropyl)piperazine (2.12 g) were dissolved in 1,4-dioxane (20 ml) and the mixture was stirred at room temperature for 4 hours. 1,4-dioxane was removed and the residue was purified by silica gel column chromatography (ethyl acetate), followed by recrystallization of the resultant from ethyl acetate-hexane to obtain 2.47 g of N-(3-(4-(diphenylmethyl)piperazinyl)propyl)(2-aminophenyl)formamide. Yield: 92%.

Workup

  1. custom1,4-dioxane was removed
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate)
  3. customfollowed by recrystallization of the resultant from ethyl acetate-hexane

Sources & evidence

ORD record
ord-24af33d7374849eb8691d1a5f3f93836
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

Loading…