Dimethylformamide → tert-Butyl 4-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate

HRID 1867576Notes

Reaction equation

HRID 1867576 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][CH2:17][CH2:18]Cl)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C[N:21](C)[CH:22]=[O:23]>>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:17][CH2:18][NH:21][C:22]2=[O:23])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 68566485HCID 68566485, compound

Product 1

HCID 46344059tert-Butyl 4-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate

Procedure

Sodium hydride (59 mg, 60% dispersion in oil, 1.5 mmol) was added to a solution of 1-t-butoxycarbonyl-4-(2-chloroethylamino)piperidine (305 mg, 0.98 mmol) in dimethylformamide (5 mL), and the reaction stirred at room temperature overnight. The reaction was quenched with water, filtered and purified by reverse phase HPLC(C-18, 5% to 95% 0.1% trifluoroacetic acid/acetonitrile in 0.1% aqueous trifluoroacetic acid, gradient elution), to give the title compound (30 mg). 1H NMR (500 MHz, CDCl3) □ 4.22 (br s, 3H), 3.88 (tt, J=4, 12 Hz, 1H), 3.52 (m, 2H), 3.46 (m, 2H), 2.79 (br t, 11 Hz, 2H), 1.72 (d, J=12 Hz, 2H), 1.56 (m, 2H), 1.48 (s, 9H).

Workup

  1. customThe reaction was quenched with water
  2. filtrationfiltered
  3. custompurified by reverse phase HPLC(C-18, 5% to 95% 0.1% trifluoroacetic acid/acetonitrile in 0.1% aqueous trifluoroacetic acid, gradient elution),

Sources & evidence

ORD record
ord-658327292e2a43e6afc781f0faf11969
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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