Benzene → 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-[2-hydroxy-3-(2-naphthalenyloxy)propyl]-1-piperazineacetamide dihydrochloride monohydrate

HRID 35338

Reaction equation

HRID 35338 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1.[NH2:16][C:17]([CH:19]1[NH:24][CH2:23][CH2:22][N:21]([CH2:25][C:26]([NH:28][C:29]2[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:36])=[O:27])[CH2:20]1)=[O:18].C1C=CC=CC=1>CO>[OH2:11].[ClH:35].[ClH:35].[NH2:16][C:17]([CH:19]1[N:24]([CH2:15][CH:13]([OH:14])[CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:23][CH2:22][N:21]([CH2:25][C:26]([NH:28][C:29]2[C:30]([Cl:36])=[CH:31][CH:32]=[CH:33][C:34]=2[Cl:35])=[O:27])[CH2:20]1)=[O:18]

Participants

5

Reactant 3

HCID 241BenzeneHCID 929952-Naphthyl glycidyl etherHCID 142302313-Carbamoyl-N-(2,6-dichlorophenyl)piperazine-1-acetamide

Product 1

HCID 704185743-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-[2-hydroxy-3-(2-naphthalenyloxy)propyl]-1-piperazineacetamide dihydrochloride monohydrateYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.5 parts of [(2-naphthalenyloxy)methyl]oxirane, 3.31 parts of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide, 45 parts of benzene and 20 parts of methanol was stirred first for 3 hours at room temperature and further for 30 hours at reflux. The reaction mixture was cooled and purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol and acetonitrile. Upon stirring overnight, the salt was filtered off and dried over week-end, yielding 1.39 parts (23%) of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-[2-hydroxy-3-(2-naphthalenyloxy)propyl]-1-piperazineacetamide dihydrochloride monohydrate; mp. 155.3° C. (compound 69).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was cooled
  3. custompurified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. stirringUpon stirring overnight
  8. filtrationthe salt was filtered off
  9. customdried over week-end

Sources & evidence

ORD record
ord-5cf3c417ac1046fe92a55f4e3df94190
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Linked notes

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