Methanol → N-(4-Chlorophenyl)-4-{[(2R)-4-ethylpiperazin-2-yl]carbonyl}piperazine-1-carboxamide

HRID 603188Notes

Reaction equation

HRID 603188 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[C@@H:12]([C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[CH2:11]1)[CH3:9].[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1.CO>ClCCl>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]([N:28]2[CH2:27][CH2:26][N:25]([C:23]([C@H:12]3[CH2:11][N:10]([CH2:8][CH3:9])[CH2:15][CH2:14][NH:13]3)=[O:24])[CH2:30][CH2:29]2)=[O:40])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 57656637tert-butyl (2R)-4-ethyl-2-(piperazin-1-ylcarbonyl)piperazine-1-carboxylate

Product 1

HCID 57656705N-(4-Chlorophenyl)-4-{[(2R)-4-ethylpiperazin-2-yl]carbonyl}piperazine-1-carboxamideYield 115.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (29 uL) was added to a solution of tert-butyl (2R)-4-ethyl-2-(piperazin-1-ylcarbonyl)piperazine-1-carboxylate (67.5 mg) in dry dichloromethane (5 ml) followed by 4-chloro phenylisocyanate (35 mg) and the reaction was stirred for 18 h under argon. Methanol (1 ml) was added, the solvent was evaporated and the product purified by chromatography (3-15% MeOH-DCM) to afford the homologated product (91 mg) as a foam. The foam was then dissolved in TFA/DCM (1:1, 6 ml) and stirred for 1 h. The solvent was removed under reduced pressure then taken up in 1M. aqueous sodium hydroxide (30 ml) and extracted with dichloromethane (2×30 ml). The combined organic layers were dried (MgSO4), filtered and evaporated to form the title compound (70 mg) as a white foam.

Workup

  1. customthe solvent was evaporated
  2. customthe product purified by chromatography (3-15% MeOH-DCM)

Sources & evidence

ORD record
ord-bf0a84b0aebd4fbcbb87aa87abf9d9e2
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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