Benzhydrylamine → HCID 20253232, compound

HRID 638097Notes

Reaction equation

HRID 638097 reaction equation
Br[CH:2]([CH:6]([CH2:9]Br)[CH2:7][CH3:8])[C:3]([OH:5])=[O:4].[CH:11]([NH2:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[C:18]1([CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:24]2[CH2:9][CH:6]([CH2:7][CH3:8])[CH:2]2[C:3]([OH:5])=[O:4])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 7036BenzhydrylamineHCID 53709889HCID 53709889, compound

Product 1

HCID 20253232HCID 20253232, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.5 g of 2A and 29 g of benzhydrylamine in acetonitrile were stirred and refluxed for 48 hours. The resulting mixture was cooled, filtered free of insoluble amine salt and the filtrate evaporated to dryness. The residue, which was a complex mixture of product, was partially purified using a column of silica gel and petroleum ether/ethyl acetate as the eluent. The first fast-running products to emerge were collected and evaporated to dryness, leaving the benzyl ester of 1-diphenylmethyl-2-carboxy-3-ethylazetidine (2B) as the major component (65% by NMR) of the crude residual mixture.

Workup

  1. temperaturerefluxed for 48 hours
  2. temperatureThe resulting mixture was cooled
  3. filtrationfiltered free of insoluble amine salt
  4. customthe filtrate evaporated to dryness
  5. additiona complex mixture of product
  6. customwas partially purified
  7. customThe first fast-running products to emerge were collected
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-0d0ac657639d47f9bcf68b45efd9f344
Source dataset
uspto-grants-1985_12
Patent number
US04560401

Reaction notes

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