HCID 1098618, compound → Benzhydrylamine

HRID 1058203Notes

Reaction equation

HRID 1058203 reaction equation
C[O-].[Na+].CO.[N+](C1C=CC=CC=1S([NH:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)=O)([O-])=O>O1CCOCC1>[CH:19]([NH2:18])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 1098618HCID 1098618, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 7036BenzhydrylamineYield 102.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 28% sodium methoxide/methanol solution (0.34 ml; 1.52 molar equivalents) was added to a solution of N-(2-nitrobenzenesulfonyl)benzhydrylamine (401.6 mg) in dry dioxane (3 ml) at room temperature in an argon atmosphere, followed by stirring for 23 hours at room temperature. The reaction solvents were removed by evaporation under reduced pressure, and water (10 ml), 2 N sulfuric acid (1.5 ml) and ether (15 ml) were added to the resulting concentrate, followed by extraction and solution separation. The organic layer was extracted again with water (5 ml). To the resulting aqueous layer, 5 N sodium hydroxide (1 ml) was added, and extraction was conducted twice with ether (13 ml), followed by drying over sodium sulfate, filtration, concentration and drying under vacuum to obtain benzhydrylamine (205.2 mg; yield: quantitative).

Workup

  1. customThe reaction solvents were removed by evaporation under reduced pressure, and water (10 ml), 2 N sulfuric acid (1.5 ml) and ether (15 ml)
  2. additionwere added to the resulting
  3. concentrationconcentrate
  4. extractionfollowed by extraction and solution separation
  5. extractionThe organic layer was extracted again with water (5 ml)
  6. additionTo the resulting aqueous layer, 5 N sodium hydroxide (1 ml) was added
  7. extractionextraction
  8. dry with materialby drying over sodium sulfate, filtration, concentration
  9. customdrying under vacuum

Sources & evidence

ORD record
ord-f26ec69b625c4a7aadbeacc03b6ff245
Source dataset
uspto-grants-2003_02
Patent number
US06515179B2

Reaction notes

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