Water → HCID 86705490, compound

HRID 2279480Notes

Reaction equation

HRID 2279480 reaction equation
FC(F)(F)S(O[C@H:7]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:8]([F:11])([F:10])[F:9])(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:38][NH2:39])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].O>C1CCCCC1>[Cl:19][C:14]1[CH:13]=[C:12]([CH:7]([NH:39][CH2:38][C:32]2[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:30]([O:29][CH3:28])[CH:31]=2)[C:8]([F:11])([F:10])[F:9])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79832VeratrylamineHCID 86705488HCID 86705488, compound

Product 1

HCID 86705490HCID 86705490, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of 144 (10.9 g, 28.9 mmol), K2CO3 (5.99 g, 43.4 mmol) and (3,4-dimethoxyphenyl)methanamine (6.77 g, 40.5 mmol) in cyclohexane (200 mL) and heated to 65° C. for 24 h. Water was added and the organic layer was concentrated and the crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (5 to 20% EtOAc) to afford 4.11 g (36.1%) of 1-(3,4-dichlorophenyl)-N-(3,4-dimethoxybenzyl)-2,2,2-trifluoroethanamine (146).

Workup

  1. concentrationthe organic layer was concentrated
  2. customthe crude product was purified by SiO2 chromatography
  3. washeluting with EtOAc/hexane (5 to 20% EtOAc)

Sources & evidence

ORD record
ord-e2b442d0f8da4268a2c17fc8e243c63e
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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