2-((1-Naphthalenyloxy)methyl)oxirane → 1-[2-Hydroxy-3-(1-naphthalenyloxy)propyl]-4-[4-[(methylsulfonyl)amino]benzoyl]piperazine

HRID 728830Notes

Reaction equation

HRID 728830 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[CH3:16][S:17]([NH:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1)(=[O:19])=[O:18]>CO>[OH:1][CH:3]([CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[CH2:2][N:30]1[CH2:31][CH2:32][N:27]([C:25](=[O:26])[C:24]2[CH:33]=[CH:34][C:21]([NH:20][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:22][CH:23]=2)[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 147398841-[4-[(Methylsulfonyl)amino]benzoyl]piperazine

Product 1

HCID 147398851-[2-Hydroxy-3-(1-naphthalenyloxy)propyl]-4-[4-[(methylsulfonyl)amino]benzoyl]piperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 7.89 g (42.4 mmol) of 1,2-epoxy-3-(1-naphthalenyloxy)propane to a solution of 12.0 9 (42.4 mmol) of 1-[4-[(methylsulfonyl)amino]benzoyl]piperazine in methanol. Heat the resultant solution at reflux for about 46 h. Cool the solution to room temperature and evaporate the solvent. Triturate the residue with ether toobtain crystals of the title compound.

Workup

  1. temperatureat reflux for about 46 h
  2. customevaporate the solvent
  3. customTriturate the residue with ether toobtain crystals of the title compound

Sources & evidence

ORD record
ord-eecd2b2f781d4955ac837ac98093689d
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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