Benzhydrylamine → HCID 70491957, compound

HRID 638101Notes

Reaction equation

HRID 638101 reaction equation
Br[CH:2]([CH:13]([CH3:16])[CH2:14]Br)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH2:17][CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:6]([O:5][C:3]([C@H:2]1[C@@H:13]([CH3:16])[CH2:14][N:17]1[CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 20253229HCID 20253229, compound

Product 1

HCID 70491957HCID 70491957, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 23.94 g of 3D, 37.6 g of aminodiphenylmethane and 170 ml of acetonitrile was refluxed for 40 hours. The mixture was cooled, filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in the minimum amount of methylene chloride, the solution was filtered through a short column of silica gel, using a 2:1 v:v mixture of hexane and ether as eluent. The solvents were evaporated. The residue was subjected to high pressure liquid chromatography (HPLC) twice, using an 8:1 v:v mixture of hexane and ether as eluent. The less polar portions thus obtained were combined, the solvents were evaporated and the residue crystallized from methylene chloride/hexane to give N-diphenylmethyl-cis-3-methyl-2-azetidinecarboxylic acid benzyl ester (3E), as a colorless solid, 112°-113.5° C.

Workup

  1. temperaturewas refluxed for 40 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in the minimum amount of methylene chloride
  6. filtrationthe solution was filtered through a short column of silica gel
  7. additionv mixture of hexane and ether as eluent
  8. customThe solvents were evaporated
  9. additionv mixture of hexane and ether as eluent
  10. customThe less polar portions thus obtained
  11. customthe solvents were evaporated
  12. customthe residue crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-a922a3ff71614a1ab8c42a6aedfd7787
Source dataset
uspto-grants-1985_12
Patent number
US04560401

Reaction notes

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