Triphenylphosphine → 4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzenemethanamine

HRID 1425710Notes

Reaction equation

HRID 1425710 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([C:33]([F:36])([F:35])[F:34])[N:32]=[N:31]2)=[CH:26][CH:25]=1)=[N+]=[N-]>C1COCC1>[F:36][C:33]([F:34])([F:35])[C:30]1([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][NH2:20])=[CH:29][CH:28]=2)[N:31]=[N:32]1

Participants

4

Reactant 2

HCID 11776Triphenylphosphine2×HCID 858170813-[4-(Azidomethyl)phenyl]-3-(Trifluoromethyl)-3H-Diazirine

Product 1

HCID 109328304-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzenemethanamineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine polymer bound (Fluka, cat #93094) (1.6 g/mol, 6.3 mmol) was added to an aqueous (378 μL, 21.0 mmol)/THF (10 mL) solution of 3-[4-(azidomethyl)phenyl]-3-(trifluoromethyl)-3H-diazirine (506 mg, 2.1 mmol). The mixture was shaken until the starting material was no longer evident by TLC analysis (18 h). The triphenylphosphine-based support was filtered, washed with CH2Cl2, and the filtrate was concentrated in vacuum to obtain 350 mg (80%) of a yellow oil corresponding to the free amine: 1H NMR (CDCl3) δ 1.35-1.50 (br s, NH2), 3.89 (s, CH2), 7.17 (d, J=8.2 Hz, 2 C6H4), 7.35 (d, J=8.2 Hz, 2 C6H4); 13C NMR (CDCl3): δ 28.4 (q, J=39.9 Hz, C diazirine), 45.9 (CH2NH2), 122.2 (q, J=273.2 Hz, CF3), 126.7 (C6H2), 127.5 (C6H2), 145.0 (C6H2) (one peak is overlapped with an other one).

Workup

  1. customwas no longer evident by TLC analysis (18 h)
  2. filtrationwas filtered
  3. washwashed with CH2Cl2
  4. concentrationthe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-623448c257da45cab6e813125eb7706f
Source dataset
uspto-grants-2015_01
Patent number
US08933065B2

Reaction notes

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