Hydrazine hydrate (1:1) → HCID 22609525, compound

HRID 1250958Notes

Reaction equation

HRID 1250958 reaction equation
O.NN.[CH3:4][O:5][C:6]1[CH:7]=[C:8](/[CH:16]=[CH:17]/[CH:18]=[CH:19]/[C:20]([N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:45])/[CH:29]=[CH:30]/[CH:31]=[CH:32]/[C:33]3[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH3:42])=[C:35]([O:43][CH3:44])[CH:34]=3)[CH2:24][CH:23]2[CH2:46][N:47]2C(=O)C3=CC=CC=C3C2=O)=[O:21])[CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13]>CO>[NH2:47][CH2:46][CH:23]1[CH2:24][N:25]([C:28](=[O:45])/[CH:29]=[CH:30]/[CH:31]=[CH:32]/[C:33]2[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH3:42])=[C:35]([O:43][CH3:44])[CH:34]=2)[CH2:26][CH2:27][N:22]1[C:20](=[O:21])/[CH:19]=[CH:18]/[CH:17]=[CH:16]/[C:8]1[CH:7]=[C:6]([O:5][CH3:4])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22609550HCID 22609550, compound

Product 1

HCID 22609525HCID 22609525, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1.3 ml (26 mmol) of hydrazine hydrate in methanol (2 ml) was added to a suspension of 430 mg (0.58 mmol) of N-[1,4-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-2-piperazinylmethyl]phthalimide synthesized by the process described in Example 48 in methanol (8 ml), and the mixture was stirred for 17 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the resultant residue was extracted with chloroform. An organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel to obtain 232 mg (yield: 65%) of 2-aminomethyl-1,4-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]piperazine as a pale yellow amorphous powder.

Workup

  1. customsynthesized by the process
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe resultant residue was extracted with chloroform
  4. washAn organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c2656db8edf9408387251872ba658d9d
Source dataset
uspto-grants-2002_01
Patent number
US06340682B1

Reaction notes

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