Hydrochloric Acid → 1-(Diphenylmethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxylic acid

HRID 1808977Notes

Reaction equation

HRID 1808977 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]2[CH2:11][C:10]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:12]#N)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:28].[Na+].[OH2:30].Cl>C(O)C>[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]2[CH2:11][C:10]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:12]([OH:30])=[O:28])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 219057811-Benzhydryl-3-benzylaminoazetidine-3-carbonitrile

Product 1

HCID 219058151-(Diphenylmethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the 1-(diphenylmethyl)-3-[(phenylmethyl)amino]azetidine-3-carbonitrile (0.80 g, 2.2 mmol), prepared using procedures similar to those described in Kozikowski and Fauq Synlett 1991, 11, 783-4, in ethanol (30 mL) was added solid sodium hydroxide (7.5 mmol), and the resulting mixture was stirred at room temperature for 3 days. Water (6 mL) was added to the reaction mixture and stirring was continued at 90° C. for 2 h. The pH of the reaction mixture was adjusted to 5 with concentrated hydrochloric acid and a white solid precipitated. The mixture was cooled, diluted with water (50 mL) and the solid was collected, washed with water then dried in vacuo to give the 1-(diphenylmethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxylic acid (0.75 g, 88% yield), MS (EI) for C24H24N2O2: 373 (MH+).

Workup

  1. stirringstirring
  2. waitwas continued at 90° C. for 2 h
  3. customa white solid precipitated
  4. temperatureThe mixture was cooled
  5. additiondiluted with water (50 mL)
  6. customthe solid was collected
  7. washwashed with water
  8. customthen dried in vacuo

Sources & evidence

ORD record
ord-0167dd3f3d5d4aec859641d4155c9522
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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