Triethylamine → 1-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

HRID 444943Notes

Reaction equation

HRID 444943 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](=O)[CH3:4].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(OCC)C.CCCCCC.Cl[Ti](Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:15]=[C:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 9871Methyl trifluoromethyl ketoneHCID 754524-Methoxybenzylamine

Product 1

HCID 866576701-(4-methoxyphenyl)-N-(1,1,1-trifluoropropan-2-ylidene)methanamine

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirring solution of trifluoroacetone (7.75 g, 69.2 mmol) in diethyl ether (60 ml) at −40° C. was added 4-methoxybenzyl amine (9.49 g, 69.2 mmol) and triethylamine (14 g, 138 mmol) in diethyl ether (40 ml). A cooled (0° C.) mixture of TiCl4 (6.56 g, 34.6 mmol) in hexane (40 ml) at was added dropwise over 10 minutes and the resulting mixture was allowed to warm up to ambient temperature over 20 mins and stirred at 50° C. for 2.5 h. The inorganic precipitate was removed by filtration and washed with diethyl ether. The filtrate was concentrated in vacuo to afford a yellow oil. Purification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane afforded the title product.

Workup

  1. temperatureA cooled
  2. additionat was added dropwise over 10 minutes
  3. customThe inorganic precipitate was removed by filtration
  4. washwashed with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a yellow oil
  7. customPurification of the crude product by chromatography on silica eluting with 0% to 25% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-c5f5c3f1a23e459cba49f4438520141d
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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