4-Amino-1,2-bis(4-methoxyphenylmethyl)pyrazolidine → 4-geranyloxy-N-[1,2-bis(4-methoxyphenylmethyl)-4-pyrazolidinyl]benzamide

HRID 1458295Notes

Reaction equation

HRID 1458295 reaction equation
[NH2:1][CH:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:3]1.[CH2:25]([O:35][C:36]1[CH:48]=[CH:47][C:39]([C:40](C2NC=CN=2)=[O:41])=[CH:38][CH:37]=1)/[CH:26]=[C:27](/[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])\[CH3:28]>O>[CH2:25]([O:35][C:36]1[CH:37]=[CH:38][C:39]([C:40]([NH:1][CH:2]2[CH2:6][N:5]([CH2:7][C:8]3[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=3)[N:4]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[CH2:3]2)=[O:41])=[CH:47][CH:48]=1)/[CH:26]=[C:27](/[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])\[CH3:28]

Participants

4

Reactant 2

HCID 221019084-Amino-1,2-bis(4-methoxyphenylmethyl)pyrazolidineHCID 699665044-Geranyloxybenzoylimidazole

Product 1

HCID 699637014-geranyloxy-N-[1,2-bis(4-methoxyphenylmethyl)-4-pyrazolidinyl]benzamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-amino-1,2-bis(4-methoxyphenylmethyl)pyrazolidine (0.80 g) in tetrahydrofuran anhydride (20 ml) was added 4-geranyloxybenzoylimidazole (0.79 g). The mixture was stirred at room temperature for one night. The reaction solution, with water added thereto, was extracted with ethyl acetate. The extract was concentrated under a vacuum and the residue was purified by silica gel column chromatography (chloroform) and then recrystallized from ethyl acetate, thereby yielding 0.65 g (45%) of the aimed compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. concentrationThe extract was concentrated under a vacuum
  3. customthe residue was purified by silica gel column chromatography (chloroform)
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e743707e77a142c596f6daaf74cbd375
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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