Sodium Hydroxide → 6-Chloro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one

HRID 2064053Notes

Reaction equation

HRID 2064053 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][CH2:12]3)[C:6]=2[CH:22]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 13792190Ethyl 4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

Product 1

HCID 137921086-Chloro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-oneYield 76.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

D7 (12.0 g, 37 mmol) was suspended in a 2.5 M aqueous solution of sodium hydroxide (150 mL). The suspension was refluxed for 15 hours and then allowed to cool. The solution was acidified with 6 M HCl (˜70 mL) until no more effervescence was observed (˜pH 2) and then the pH was carefully adjusted to pH 8.5 using 2.5M aqueous NaOH whilst the solution was cooled to 0° C. The resulting precipitate was collected by filtration, washed with cold water (20 mL) and then dried under vacuum at 40° C. for 15 hours to give the title compound (7.1 g, 76% yield) as a light brown solid (Rf: Baseline (ethyl acetate)). 1H-NMR (300 MHz, DMSO-d6) □ 11.11 (1H, br s), 8.97 (1H, br s), 7.52 (1H, s), 6.99-6.97 (2H, m), 4.51-4.48 (1H, m), 3.33-3.31 (2H, m), 3.02-2.97 (2H, m), 2.48-2.46 (2H, m), 1.81-1.77 (2H, m); m.p.>300° C.

Workup

  1. temperatureThe suspension was refluxed for 15 hours
  2. temperatureto cool
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with cold water (20 mL)
  5. customdried under vacuum at 40° C. for 15 hours

Sources & evidence

ORD record
ord-d96671cc35674a76b1df376ce1dd926b
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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