Sodium Hydroxide → HCID 178518598, compound

HRID 2294917Notes

Reaction equation

HRID 2294917 reaction equation
C(C([N:7]1[CH2:12][CH2:11][N:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1)=O)(C)(C)C.[OH-].[Na+]>Cl>[N:10]1([C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178447193HCID 178447193, compound

Product 1

HCID 178518598HCID 178518598, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 0.52 g of 1,3-dihydro-1-{trans-4-[4-(tert-butylcarbonyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one in 15 mL of 1N HCl was heated to reflux for 1 h, cooled and basified with 6N NaOH. The basic mixture was extracted with 2×50 mL portions of chloroform. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. After drying overnight under vacuum, there was obtained 0.28 g of 1,3-dihydro-1-{trans-4-[1-piperazinyl]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: 1H NMR (400 MHz, CDCl3) 7.16-7.03 (m, 4H), 4.27 (m, 1H), 2.94 (m, 4H), 2.61 (m, 4H), 2.25 (m, 2H), 2.1 (d, 2H), 1.97 (d, 2H), 1.54 (m, 2H).

Workup

  1. temperatureto reflux for 1 h
  2. temperaturecooled
  3. extractionThe basic mixture was extracted with 2×50 mL portions of chloroform
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customAfter drying overnight under vacuum

Sources & evidence

ORD record
ord-60332590c7e84ab99303b1bead4a5bce
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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