Diisopropylethylamine → 1-(2-(4-Benzyl-piperazin-1-yl)-ethyl)-3-(2,4,6-trimethyl-3-piperidin-1-yl-phenyl)-urea

HRID 2251310Notes

Reaction equation

HRID 2251310 reaction equation
[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12]N[CH2:10][CH2:9]2)=[C:6]([CH3:14])[CH:5]=[C:4]([CH3:15])[C:3]=1[NH2:16].[CH3:17]CN(C(C)C)C(C)C.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[CH2:38]([N:45]1[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][NH2:53])[CH2:47][CH2:46]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCCl>[CH2:38]([N:45]1[CH2:46][CH2:47][N:48]([CH2:51][CH2:52][NH:53][C:30]([NH:16][C:3]2[C:4]([CH3:15])=[CH:5][C:6]([CH3:14])=[C:7]([N:8]3[CH2:9][CH2:10][CH2:17][CH2:12][CH2:13]3)[C:2]=2[CH3:1])=[O:36])[CH2:49][CH2:50]1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 27353312-(4-Benzylpiperazin-1-yl)ethan-1-amineHCID 47388012,4,6-Trimethyl-3-piperazin-1-yl-phenylamine

Product 1

HCID 596437401-(2-(4-Benzyl-piperazin-1-yl)-ethyl)-3-(2,4,6-trimethyl-3-piperidin-1-yl-phenyl)-ureaYield 166.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 2,4,6-trimethyl-3-piperazin-1-yl-phenylamine (0.2 g, 0.92 mmol) and Hunig's base (0.7 mL, 4.0 mmol) in anhydrous 1,2-dichloroethane (3 mL) at 0° C. was added triphosgene (0.1 g, 0.35 mmol). The mixture was stirred at 0° C. for 30 minutes before the addition of a solution of 2-(4-benzyl-piperazin-1-yl)-ethylamine (0.2 g, 0.92 mmol) in 1,2-dichloroethane (2 mL). The reaction was stirred overnight and partitioned between water and methylene chloride. The organic layer was washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed with florisil, eluting with a mixture of hexanes and ethyl acetate in the ratio of 2:1 to 100% ethyl acetate, and then to a mixture of ethyl acetate and MeOH (30:1) to give the title compound as a white foam (0.27 g, 64% yield).

Workup

  1. custompartitioned between water and methylene chloride
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed with florisil
  6. washeluting with a mixture of hexanes and ethyl acetate in the ratio of 2
  7. addition1 to 100% ethyl acetate, and then to a mixture of ethyl acetate and MeOH (30:1)

Sources & evidence

ORD record
ord-f48263cced8543fe96b08f1b5e03a90e
Source dataset
uspto-grants-2008_01
Patent number
US07319111B2

Reaction notes

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