Benzylamine → N-benzyl-1,1,1-trifluoro-3-nitropropan-2-amine

HRID 711510Notes

Reaction equation

HRID 711510 reaction equation
[F:1][C:2]([F:9])([F:8])[CH:3]=[CH:4][N+:5]([O-:7])=[O:6].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[CH2:10]([NH:17][CH:3]([CH2:4][N+:5]([O-:7])=[O:6])[C:2]([F:9])([F:8])[F:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 2206333,3,3-Trifluoro-1-nitropropene

Product 1

HCID 58317625N-benzyl-1,1,1-trifluoro-3-nitropropan-2-amineYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,3,3-trifluoro-1-nitroprop-1-ene (4 g, 28.4 mmol) and benzylamine (3.2 g, 30.0 mmol) in toluene (50 mL) was stirred for RT or 1 h. The mixture was concentrated and the residue was purified by column chromatography (EtOAc/PE=1/10) to give the title compound (5.5 g, 78%). 1H NMR (400 MHz, CDCl3) δ ppm 3.91-3.95 (m, 1H), 4.06-4.14 (m, 1H), 4.45-4.51 (m, 1H), 4.63-4.67 (m, 1H), 7.30-7.39 (m, 5H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography (EtOAc/PE=1/10)

Sources & evidence

ORD record
ord-702c159211ac44b09b54ae93aae51a2e
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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