1,1'-Carbonyldiimidazole → tert-Butyl 4-[2-({4-chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoyl}amino)ethyl]-1-piperazinecarboxylate

HRID 412010Notes

Reaction equation

HRID 412010 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)=[O:8])=[C:4]([O:11][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:3]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylateHCID 112539014-Chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoic acid

Product 1

HCID 11282784tert-Butyl 4-[2-({4-chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoyl}amino)ethyl]-1-piperazinecarboxylateYield 48.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The product from step (b) (0.7 g) and 1,1′-carbonyldiimidazole (0.62 g) were dissolved in N,N-dimethylformamide (10 ml) and stirred at room temperature for 1 hour. tert-Butyl 4-(2-aminoethyl)-1-piperazinecarboxylate (2.73 g) was added, the solution stirred for 16 hours and then evaporated to leave a gum. Dichloromethane and sodium bicarbonate solution were added, the organic phase was separated, dried and concentrated to a gum which was purified by chromatography (ethyl acetate:triethylamine, 10:1) to give the product as a solid (0.62 g), m.p. 139-140° C.

Workup

  1. stirringthe solution stirred for 16 hours
  2. customevaporated
  3. customto leave a gum
  4. customthe organic phase was separated
  5. customdried
  6. concentrationconcentrated to a gum which
  7. customwas purified by chromatography (ethyl acetate:triethylamine, 10:1)

Sources & evidence

ORD record
ord-993fa7ad964a47cc86158dfba81b731d
Source dataset
uspto-grants-2003_05
Patent number
US06562825B1

Reaction notes

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