Acetone → HCID 86681371, compound

HRID 1406670Notes

Reaction equation

HRID 1406670 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1)=[CH2:2].Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])(O)=O.[Na+].CC(C)=O>C(Cl)(Cl)Cl>[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:13]2)=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7751Ethyl chloroacetateHCID 516892Sodium BicarbonateHCID 33328804-(Piperazinylmethyl)styrene

Product 1

HCID 86681371HCID 86681371, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Synthesized according to General Procedure B: 8 (5.33 g, 26.4 mmol, 1 equiv.), ethyl chloroacetate (3.1 mL, 29.0 mmol, 1.1 equiv.), NaHCO3 (2.77 g, 33.0 mmol, 1.25 equiv.), acetone (52.8 mL), chloroform (30.0 mL). Purification with flash column chromatography on silica gel (1:1 hexanes:EtOAc) afforded 9 (3.31 g, 70%) as an orange oil. 1H-NMR (500 MHz, CDCl3): δ 7.35 (d, 2H, J=8.0 Hz), 7.26 (d, 2H, J=8.0 Hz), 6.69 (dd, 1H, J=11.0, 17.5 Hz), 5.72 (dd, 1H, J=0.5, 17.5 Hz), 5.21 (dd, 1H, J=1.0, 11.0 Hz), 4.17 (q, 2H, J=7.0 Hz), 3.49 (s, 2H), 3.19 (s, 2H), 2.59 (br s, 4H), 2.52 (br s, 4H), 1.26 (t, 3H, J=7.0 Hz). 13C-NMR (125 MHz, CDCl3): δ 170.2, 137.7, 136.5, 136.4, 129.3, 126.0, 113.4, 62.6, 60.5, 59.5, 53.0, 52.7, 14.2.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-9f134f08f85947a5ad4458606b018e6c
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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