Trifluoroacetic acid → HCID 19775301, compound

HRID 1613185Notes

Reaction equation

HRID 1613185 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]([OH:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:22][C:23]([CH3:27])([CH3:26])[CH2:24]O>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][O:21][CH:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7037BenzhydrolHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 19775301HCID 19775301, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (25 ml) was added to a solution of benzhydrol (9.2 g) and 2-amino-2-methylpropanol (4.5 g) in methylene chloride (5 ml) and the mixture was stirred at room temperature for 3 hours and evaporated. The residue was partitioned between water and ethyl acetate and the organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was triturated with hexane and recrystallised from ethyl acetate to give the title compound as a colourless solid (2.98 g, 16%), m.p. 160°-161°.

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated with hexane
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-657f2f0410d84a95a0880a978bafa5af
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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