1,2-Dichloroethane → 1-Cyclopentyl-4-[1-tert-butoxycarbonyl-piperidine-4-carbonyl]-piperazine

HRID 734318Notes

Reaction equation

HRID 734318 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[CH:31]1([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32]1>CN(C=O)C>[CH:31]1([N:36]2[CH2:37][CH2:38][N:39]([C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]3)=[O:16])[CH2:40][CH2:41]2)[CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 8064211-Cyclopentylpiperazine

Product 1

HCID 688192131-Cyclopentyl-4-[1-tert-butoxycarbonyl-piperidine-4-carbonyl]-piperazineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-tert-Butoxycarbonyl-piperidine-4-carboxylic acid (2.2 g) in dry DMF (40 ml) was treated with EDC (3.71 g) followed by HOAT (0.1 g). After 5 min, N-cyclopentylpiperazine (1.5 g) in dry DMF (5 ml) was added and the reaction mixture was stirred at rt for 18 h. Excess DMF was removed by evaporation and the resulting residue was re-dissolved in DCM, adsorbed onto silica gel (10 g) and purified by chromatography [silica gel 0-10% MeOH (containing 10% 0.88 ammonia solution/DCM)]. The pure fractions were combined and the solvent removed by evaporation to give the subtitled compound (2 g). LCMS electrospray(+ve) 366(MH+).

Workup

  1. customExcess DMF was removed by evaporation
  2. dissolutionthe resulting residue was re-dissolved in DCM
  3. custompurified by chromatography [silica gel 0-10% MeOH (containing 10% 0.88 ammonia solution/DCM)]
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-0ec679d053724f9b9eb1eba83732442c
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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