Nitrogen → HCID 12509143, compound

HRID 239813Notes

Reaction equation

HRID 239813 reaction equation
[C:1]1([N:7]2[C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C@@H:8]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N#N>C1(C)C=CC=CC=1>[C:16]1([CH:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 947NitrogenHCID 1550757cis-1,2,3-Triphenylaziridine

Product 1

HCID 12509143HCID 12509143, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a glove box, tBu2PH(C6F4)BH(C6F5)2 (0.33 g, 0.05 mmol) and cis-1,2,3-triphenylaziridine (0.271 g, 1.0 mmol) were weighed into a 100 ml round bottomed glass flask equipped with a Kontes valve and a magnetic stirbar. Toluene (4 ml) is added, the reaction transferred to a vacuum/H2 line and the mixture is freeze-pump-thaw cycled three times. The mixture is cooled to −196° C. (liquid N2) and 1 atm. H2 is introduced. The flask is sealed, the reaction is placed in a 120° C. preheated bath and rapidly (500 rpm) stirred. The reaction is periodically monitored by 1H NMR spectroscopy and is complete in 2 hours. The reaction mixture is poured onto a small plug of silica and eluted with 2:1 hexanes/ethyl acetate (50 ml). The solvent is removed in vacuo and the product N-1,2-diphenylethyl-N-phenyl amine isolated. Yield: 0.269 g (98%)

Workup

  1. customequipped with a Kontes valve
  2. additionH2 is introduced
  3. customThe flask is sealed
  4. customis placed in a 120° C.
  5. additionThe reaction mixture is poured onto a small plug of silica
  6. washeluted with 2:1 hexanes/ethyl acetate (50 ml)
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-db855be05a5c435eb8609e7288932c8f
Source dataset
uspto-grants-2014_02
Patent number
US08642812B2

Reaction notes

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