Ethanol → 1-benzhydrylazetidine-2-carboxylic Acid

HRID 1731238Notes

Reaction equation

HRID 1731238 reaction equation
[CH:1]([N:14]1CC[CH:15]1[CH2:18]C#N)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:21].[Na+].[CH2:23]([OH:25])[CH3:24]>O>[CH:1]([N:14]1[CH2:15][CH2:18][CH:24]1[C:23]([OH:21])=[O:25])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20228404[1-(Diphenylmethyl)azetidin-2-yl]acetonitrile

Product 1

HCID 99034621-benzhydrylazetidine-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of the 1C, 2.5 g of sodium hydroxide, 36 ml of ethanol and 24 ml of water was refluxed for 6 hours, then left to cool for 16 hours. The mixture then was poured into water, washed with ether and acidified to pH 5. The solvent was evaporated, the residue was taken up in methanol, the solution was filtered and the methanol was evaporated. The residue was dissolved in chloroform; the solution was washed with brine, dried and the solvent was evaporated, to give 1-benzhydryl-2-azetidine carboxylic acid (1D).

Workup

  1. temperaturewas refluxed for 6 hours
  2. waitleft
  3. temperatureto cool for 16 hours
  4. washwashed with ether
  5. customThe solvent was evaporated
  6. filtrationthe solution was filtered
  7. customthe methanol was evaporated
  8. dissolutionThe residue was dissolved in chloroform
  9. washthe solution was washed with brine
  10. customdried
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-738cfb26eb8947e2afcca800debad3d6
Source dataset
uspto-grants-1986_11
Patent number
US04620866

Reaction notes

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