Sodium Hydroxide → HCID 178518598, compound

HRID 2294912Notes

Reaction equation

HRID 2294912 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+]>Cl>[N:11]1([C@H:14]2[CH2:19][CH2:18][C@H:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178452343HCID 178452343, compound

Product 1

HCID 178518598HCID 178518598, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 0.52 g of trans-1,3-dihydro-1-{4-[4-(tert-butyloxycarbonyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one in 15 mL of 1N HCl was heated to reflux for 1 h, cooled, basified to pH 10 with 6N NaOH and extracted 2×50 mL of CHCl3. The combined extracts were dried over MgSO4 and concentrated under reduced pressure. After drying overnight under vacuum, there was obtained 0.28 g of trans-1,3-dihydro-1-{4-(1-piperazinyl)-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: 1H NMR (400 MHz, CDCl3) 7.14 (m, 1H), 7.11 (m, 1H), 7.07 (m, 2H), 4.28 (m, 1H), 2.61 (s, 4H), 2.45 (t, 1H), 2.26 (q, 2H), 2.10 (d, J=12.2, 2H), 2.0 (d, J=10.8, 2H), 1.53 (q, 2H).

Workup

  1. temperatureto reflux for 1 h
  2. temperaturecooled
  3. extractionextracted 2×50 mL of CHCl3
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customAfter drying overnight under vacuum

Sources & evidence

ORD record
ord-4518bba858cc4c7eab1cccad7a6e6ced
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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