Diisopropylethylamine → (E)-tert-Butyl (2-(1-(3-(3,5-dichlorophenyl)acryloyl)piperidin-4-yl)ethyl)carbamate

HRID 1480422Notes

Reaction equation

HRID 1480422 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:38]([O:42][C:43](=[O:53])[NH:44][CH2:45][CH2:46][CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)([CH3:41])([CH3:40])[CH3:39].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[C:38]([O:42][C:43](=[O:53])[NH:44][CH2:45][CH2:46][CH:47]1[CH2:48][CH2:49][N:50]([C:11](=[O:13])/[CH:10]=[CH:9]/[C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:51][CH2:52]1)([CH3:41])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 64421483-(3,5-Dichlorophenyl)acrylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To (E)-3-(3,5-dichlorophenyl)acrylic acid (step 2) (1.365 g, 6.29 mmol) in NMP (12 ml) was added HATU (2.87 g, 7.55 mmol) and the mixture was stirred for 5 minutes at RT. tert-Butyl(2-(piperidin-4-yl)ethyl)carbamate (1.436 g, 6.29 mmol) was added followed by DIPEA (3.30 ml, 18.87 mmol) and stirring continued at RT overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic portion was washed with water, saturated sodium bicarbonate solution, water, brine and dried using a phase separating column and the solvent removed under reduced pressure. The crude material was purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane to afford the title compound;

Workup

  1. stirringstirring
  2. waitcontinued at RT overnight
  3. extractionextracted with EtOAc
  4. washThe organic portion was washed with water, saturated sodium bicarbonate solution, water, brine
  5. customdried
  6. customseparating column
  7. customthe solvent removed under reduced pressure
  8. customThe crude material was purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-a39cc06a43d34a06961cc79ca0617ef2
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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