Hydrazine hydrate (1:1) → HCID 22011014, compound

HRID 323151Notes

Reaction equation

HRID 323151 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:49]=[CH:48][C:20]([C:21]([N:23]([CH3:47])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:36]4C(=O)C5=CC=CC=C5C4=O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.O.NN>C(O)C.C(OCC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:47])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:22])=[CH:48][CH:49]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22010690HCID 22010690, compound

Product 1

HCID 22011014HCID 22011014, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-phthalimidopentyloxy)phenyl]benzamide (1.1 g) in ethanol (20 ml) was stirred rapidly and treated with hydrazine hydrate (844 mg). The mixture was stirred at 60° C. for 3 hours. After cooling, the reaction mixture was diluted with diethyl ether and filtered through Celite. The Celite was washed with diethyl ether, and the filtrate was concentrated. The residual milky oil was again dissolved in diethyl ether, filtered through Celite, washed with diethyl ether, and concentrated to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-aminopentyloxy)phenyl]benzamide

Workup

  1. stirringThe mixture was stirred at 60° C. for 3 hours
  2. temperatureAfter cooling
  3. filtrationfiltered through Celite
  4. washThe Celite was washed with diethyl ether
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residual milky oil was again dissolved in diethyl ether
  7. filtrationfiltered through Celite
  8. washwashed with diethyl ether
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-49c9de55c9e049e1a499f8bc0666c42d
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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