1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10632446, compound

HRID 1191005Notes

Reaction equation

HRID 1191005 reaction equation
[C:1]1([C@@H:7]([N:9]=[C:10]([CH3:15])[C:11]([F:14])([F:13])[F:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[C:1]1([C:7](=[N:9][C@H:10]([CH3:15])[C:11]([F:12])([F:13])[F:14])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10846338HCID 10846338, compound

Product 1

HCID 10632446HCID 10632446, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To crude (S)-(1-phenylethyl)-(2′,2′,2′-trifluoro-1-methylethylidene)-amine (1410 g, 4.54 mol theory) and washings with 20 g of toluene at room temperature, add DBU (1050 g, 6.897 mol) in portions to keep temperature below 60° C. Heat the reaction at 60° C. overnight (14 h) under nitrogen until the starting material rearranges to the desired intermediate (2460 g of solution). MS (ES+) m/z: 216.2 (M+H)+.

Workup

  1. customtemperature below 60° C
  2. temperatureHeat

Sources & evidence

ORD record
ord-059d9c2f2a4b4ee3b70305df26a20861
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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