Trifluoroacetic acid → 5-(Piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1397894Notes

Reaction equation

HRID 1397894 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)=[CH:10][C:4]=2[NH:3]1.FC(F)(F)C(O)=O>C(Cl)Cl.CO>[NH:14]1[CH2:13][CH2:12][CH:11]([C:9]2[CH:8]=[CH:7][C:5]3[NH:6][C:2](=[O:1])[NH:3][C:4]=3[CH:10]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117716866tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 824933395-(Piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-oneYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 17 (0.95 g, 3 mmol) in a mixture of CH2Cl2 (15 mL) and CH3OH (20 mL) was added trifluoroacetic acid (3 mL) at 0° C., and the mixture was stirred for 6 h at room temperature. Solvents were evaporated under reduced pressure, and triturating with diethyl ether gave the title compound 5. Yield: 90%, light yellow solid, mp 214-215° C. IR (KBr, cm−1) 3238 (CONH), 3043 (Ar—H), 2956 (Alph-H), 1692 (CO), 1612, 1446 (C—C), 1180 (C—N), 1126 (C-0); 1HNMR (500 MHz, DMSO d6) δ 1.73-188 (m, 3H, CH, CH2), 2.77 (m, 2H, CH2), 2.97 (m, 2H, CH2), 3.44 (obscured by H2O, 2H, CH2), 4.46 (m, 1H, CH), 6.74-6.84 (m, 3H, H-4, H-6, H-7), 10.50 (br. s, 1H, NH), 10.54 (br. s, 1H, NH). 13C NMR (125.7 MHz, DMSO d6) δ 30.04 (CH2), 33.37 (CH), 43.86 (CH2), 106.66 (C-4), 118.43 (C-7), 118.94 (C-6), 128.37 (C-8), 129.87 (C-9), 137.24 (C-5), 155.56 (CO). Anal. Calcd for C14H16F3N3O3: C, 50.76; H, 4.87; N, 12.68%. Found: C, 50.70; H, 4.92; N, 12.60%.

Workup

  1. customSolvents were evaporated under reduced pressure
  2. customtriturating with diethyl ether

Sources & evidence

ORD record
ord-16bb033e0cfc4eda8d5ec0cc39ea2c87
Source dataset
uspto-grants-2014_12
Patent number
US08901304B1

Reaction notes

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