Triphosgene → HCID 178501097, compound

HRID 538076Notes

Reaction equation

HRID 538076 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])[CH2:7][CH2:6]1)=[O:4].Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>CC#N>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH:21][C:23]2=[O:25])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 178501121HCID 178501121, compound

Product 1

HCID 178501097HCID 178501097, compoundYield 263.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of trans-4-{[2-(2-Amino-phenyl)-ethylamino]-methyl}-cyclohexanecarboxylic acid methyl ester (2.99 g, 7.97 mmol) in CH3CN (100 mL) at 0° C. under argon was added portion wise triphosgene (1.53 g, 5.15 mmol) over 30 min. The reaction mixture was stirred at 0° C. for 30 min, warmed to room temperature and stirred additionally for 7 h. Then an excess of TEA was added and a precipitate was formed. Solvent was removed under reduced pressure and the crude product purified by flash chromatography on silica to afford the titled compound (4.3 g, yield 59%).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred additionally for 7 h
  3. additionThen an excess of TEA was added
  4. customa precipitate was formed
  5. customSolvent was removed under reduced pressure
  6. customthe crude product purified by flash chromatography on silica

Sources & evidence

ORD record
ord-fb37499baefd496d898cc617bfffda8e
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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