Hydrochloric Acid → Benzhydrylamine

HRID 1058205Notes

Reaction equation

HRID 1058205 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.Cl>C(#N)C>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1098618HCID 1098618, compoundHCID 23694274Sodium methanolate methanol2×

Product 1

HCID 7036BenzhydrylamineYield 77.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 28% sodium methoxide/methanol solution (0.34 ml; 1.51 molar equivalents) was added to a solution of N-(2-nitrobenzenesulfonyl)benzhydrylamine (402.1 mg) in dry acetonitrile (3 ml) at room temperature in a nitrogen atmosphere, followed by stirring for 27 hours at room temperature. On the way, a 28% sodium methoxide/methanol solution (0.34 ml; 1.51 molar equivalents) was further added after 10 hours. The reaction mixture was cooled with ice, 1 N hydrochloric acid (5 ml) was added, and the reaction solvents were removed by evaporation under reduced pressure. Water (5 ml), 1 N hydrochloric acid (5 ml) and ether (30 ml) were added to the resulting concentrate, followed by extraction and solution separation, and the organic layer was extracted again with water (5 ml). Sodium hydroxide (0.62 g) was added to the resulting aqueous layer, and extraction was conducted three times with ether (20 ml), followed by drying over sodium sulfate, filtration, concentration and drying under vacuum to obtain benzhydrylamine (155.9 mg; yield: 77.9%).

Workup

  1. additionwas added
  2. customthe reaction solvents were removed by evaporation under reduced pressure
  3. additionWater (5 ml), 1 N hydrochloric acid (5 ml) and ether (30 ml) were added to the resulting
  4. concentrationconcentrate
  5. extractionfollowed by extraction and solution separation
  6. extractionthe organic layer was extracted again with water (5 ml)
  7. additionSodium hydroxide (0.62 g) was added to the resulting aqueous layer, and extraction
  8. dry with materialby drying over sodium sulfate, filtration, concentration
  9. customdrying under vacuum

Sources & evidence

ORD record
ord-928e060a7dbb4455bf9fd394210aa3dd
Source dataset
uspto-grants-2003_02
Patent number
US06515179B2

Reaction notes

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