Sodium Hydroxide → HCID 178518600, compound

HRID 1899901Notes

Reaction equation

HRID 1899901 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][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)[CH2:8][CH2:7]1)=O)C.[OH-].[Na+]>Cl>[NH:6]1[CH2:7][CH2:8][CH:9]([NH:12][C@H:13]2[CH2:14][CH2:15][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])[CH2:17][CH2:18]2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178473349HCID 178473349, compound

Product 1

HCID 178518600HCID 178518600, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

. A stirred solution of 1.2 g of 1,3-dihydro-1-{trans-4-[1-ethoxycarbonyl-4-piperidinylamino]-1-cyclohexyl}-2H-benzimidazol-2-one in 20 mL of 6N HCl was heated to reflux for 12 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 0.51 g of 1,3-dihydro-1-{trans -4-[4-piperidinylamino]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: 1H NMR (400 MHz, CDCl3) 7.33 (m, 1H), 7.11 (m, 1H), 7.04 (m, 2H), 4.37 (m, 1H), 3.16 (m, 3H), 2.61-2.52 (m, 5H), 2.0 (d, 2H), 1.86 (d, 2H), 1.64 (m, 4H), 1.3 (m, 2H).

Workup

  1. temperatureto reflux for 12 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-4dd68037cf6b47b5b918974c12963be1
Source dataset
uspto-grants-1996_11
Patent number
US05574044

Reaction notes

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