Triethylamine → (1-(3,5-Dichloropyridin-4-yl)piperidin-4-yl)(morpholino) methanone

HRID 1622336Notes

Reaction equation

HRID 1622336 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])[CH2:3][CH2:2]1.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[N:12]1[CH2:13][CH2:14][CH:9]([C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[O:8])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15202114-(4-Piperidinylcarbonyl)MorpholineHCID 37865313,4,5-Trichloropyridine

Product 1

HCID 45274906(1-(3,5-Dichloropyridin-4-yl)piperidin-4-yl)(morpholino) methanoneYield 36.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

General procedure C was followed using morpholino(piperidin-4-yl)methanone (21 mg, 0.12 mmol), 3,4,5-trichloropyridine (23 mg, 0.12 mmol), triethylamine (32 μL, 0.23 mmol) and NMP (1 mL). The crude product was purified by flash column chromatography on silica gel (hexane/EtOAc, 1:1) to furnish the title compound as a white solid (15 mg, 35%), m.p. 172-174° C.; umax (CHCl3)/cm−1 3006, 2858, 1632, 1559, 1448, 1116, 1020; m/z (ESI) C15H20Cl2N3O2 requires 344.0927, found [M+H]+ 344.0929.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-ecc0671a1a98432891bc44ae4536a6e2
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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