Succinic anhydride → 4-(1-Dimethylaminomethyl-1H-benzoimidazole-5-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1909050

Reaction equation

HRID 1909050 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:24]=[CH:23][C:19]3[NH:20][CH:21]=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(=O)OC(=O)CC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[CH:24]=[CH:23][C:19]3[N:20]([CH2:6][N:8]([CH3:13])[CH3:9])[CH:21]=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 11430Potassium CarbonateHCID 178452348HCID 178452348, compound

Product 1

HCID 665994174-(1-Dimethylaminomethyl-1H-benzoimidazole-5-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To stirring solution of 1 (1.50 g, 4.54 mmol) in dichloromethane (20 mL) was added potassium carbonate (690 mg, 4.99 mmol, 1.1 eq) and succinic anhydride (500 mg, 4.99 mmol, 1.1 eq) at 23° C. Next, N,N,N′,N′-tetramethylamino methane (0.68 mL, 4.99 mmol, 1.1 eq) was added dropwise and the suspension stirred at room temperature for 6 hr. The reaction mixture was diluted with dichloromethane (50 mL) and quenched with 20% NaOH (aq) (50 mL). The layers were separated and the organic washed with water, dried over Na2SO4, and concentrated to an off white solid (1.76 g, 4.74 mmol, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.94 (s, 1H), δ 7.79-7.71 (m, 1H), δ 7.60 (s, 0.5H), δ 7.50-7.48 (d, 0.5H), δ 7.38-7.35 (d, 0.5H), δ 7.25-7.22 (d, 0.5H), δ 4.80-4.78 (d, 2H), δ 3.80-3.35 (m, 8H), δ 2.28 (s, 6H), δ 1.41 (s, 9H)

Workup

  1. customquenched with 20% NaOH (aq) (50 mL)
  2. customThe layers were separated
  3. washthe organic washed with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-659c200c780044efb421358518b18abd
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Linked notes

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