Benzylamine → HCID 178506344, compound

HRID 1487493Notes

Reaction equation

HRID 1487493 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[C:9]([F:12])([F:11])[F:10])=[N:6][CH:7]=1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH2:14](/[N:21]=[C:8](\[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)/[C:9]([F:12])([F:11])[F:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 672952111-(5-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 178506344HCID 178506344, compoundYield 4.4%

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(5-Bromo-pyridin-2-yl)-2,2,2-trifluoro-ethanone (7.5 g, 29.52 mmol) in dry toluene (30 mL) is added benzylamine (3.15 g, 29.52 mmol) and titanium ethoxide (7.4 g, 32.48 mmol) at room temperature then stir for 3 hours. Reaction mixture is diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting in 20% ethyl acetate in hexane to afford the title compound (0.45 g). LC-MS (m/z): [M+H]=345.0.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by column chromatography
  6. washeluting in 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0bf2517005c946b6bb017566379d02ab
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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