Trifluoroacetic acid → (E)-1-(4-(2-Aminoethyl)piperidin-1-yl)-3-(3,5-dichlorophenyl)prop-2-en-1-one

HRID 1480423Notes

Reaction equation

HRID 1480423 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:27])/[CH:17]=[CH:18]/[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)[CH2:12][CH2:11]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:27])/[CH:17]=[CH:18]/[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722653(E)-tert-Butyl (2-(1-(3-(3,5-dichlorophenyl)acryloyl)piperidin-4-yl)ethyl)carbamate

Product 1

HCID 86722654(E)-1-(4-(2-Aminoethyl)piperidin-1-yl)-3-(3,5-dichlorophenyl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (E)-tert-butyl(2-(1-(3-(3,5-dichlorophenyl)acryloyl)piperidin-4-yl)ethyl)carbamate (step 3) (400 mg, 0.936 mmol) in DCM (5 ml) was added TFA (0.865 ml, 11.23 mmol) and the mixture was stirred at RT for 1 h. The solvent was removed under reduced pressure and the crude material was dissolved in MeOH and loaded on to an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with excess MeOH. The product was eluted using 2.0 M ammonia in MeOH and the solvent removed under reduced pressure to afford the title compound as a white solid;

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe crude material was dissolved in MeOH
  3. washThe cartridge was washed with excess MeOH
  4. washThe product was eluted
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-58e4a99a42c84cf8bbae0b975b869a2c
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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