Sodium Carbonate → HCID 89488336, compound

HRID 1485365Notes

Reaction equation

HRID 1485365 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:10]=1[CH2:11][N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH:13]1[CH3:19].F[B-](F)(F)F.[CH2:31]([O+](CC)CC)[CH3:32]>C(Cl)Cl.O>[CH3:7][O:8][C:9]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:10]=1[CH2:11][N:12]1[CH:13]([CH3:19])[C:14]([O:18][CH2:31][CH3:32])=[N:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 76453846HCID 76453846, compound

Product 1

HCID 89488336HCID 89488336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Oven-dried (115° C.) sodium carbonate (18.6 g, 98 mmol, 2.25 eq.) was placed in a 500 mL round-bottom flask. The round-bottom flask was backfilled with Ar and then capped with a rubber septum. A solution of 4-(2,4-dimethoxybenzyl)-3-methylpiperazin-2-one 1.1a (20.6 g, 78 mmol, 1 eq.) in anhydrous DCM (250 mL) was added, followed by triethyloxonium tetrafluoroborate (18.6 g, 98 mmol, 1.25 eq.) in one portion. Thereafter, the reaction mixture was stirred further at RT for 1 h whereupon the reaction mixture was diluted with water (250 mL). The aqueous layer was extracted with DCM (3×150 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude compound was then purified on silica gel (EtOAc) to afford the desired product 1a as orange oil. Yield: 13.2 g, 58%. LCMS: P=93%, retention time=1.8 min, (M+H+H2O)+: 311; 1H-NMR (CDCl3): δ 7.23 (d, J=8.8 Hz, 1H), 6.48 (d, J=8.8 Hz, 1H), 6.44 (s, 1H), 4.02 (m, 2H), 3.92 (s, 3H), 3.91 (s, 3H), 3.86 (d, JAB=14.0 Hz, 1H), 3.46 (d, JAB=14.0 Hz, 1H), 3.44 (m, 2H), 3.10 (m, 1H), 2.79 (m, 1H), 2.32 (m, 1H), 1.35 (d, J=6.8 Hz, 3H), 1.24 (t, J=6.0 Hz, 3H).

Workup

  1. customwas placed in a 500 mL round-bottom flask
  2. customcapped with a rubber septum
  3. extractionThe aqueous layer was extracted with DCM (3×150 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was then purified on silica gel (EtOAc)

Sources & evidence

ORD record
ord-fa94d073c82b4405820ae36f3411b8ff
Source dataset
uspto-grants-2016_08
Patent number
US09422299B2

Reaction notes

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