Hydrochloric Acid → 1-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(6-chlorobenzimidazol-2-on-1-yl)-piperidine

HRID 2417804Notes

Reaction equation

HRID 2417804 reaction equation
[O-:1][C:2]#N.[K+].[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH:6]1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=2[NH2:30])[CH2:18][CH2:17]1.Cl>O>[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH:6]1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([N:22]2[C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=3[NH:30][C:2]2=[O:1])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 204467041-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(5-chloro-2-aminoanilino)-piperidine

Product 1

HCID 137921481-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(6-chlorobenzimidazol-2-on-1-yl)-piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 4.8 g of potassium cyanate in 10 ml of water was added to 14.5 g of 1-[(benzo-1,4-dioxan-2-yl)-methyl]-4-(5-chloro-2-aminoanilino)-piperidine in 5 ml of 10% strength hydrochloric acid and 40 ml of water, whilst cooling and stirring. When the addition had ended, the mixture was stirred at room temperature for 1 hour and then under reflux for 24 hours. After the mixture had been cooled, it was extracted with chloroform. The extract was washed with 5% strength hydrochloric acid, dried and filtered and the filtrate was concentrated.

Workup

  1. temperaturewhilst cooling
  2. additionWhen the addition
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. temperatureunder reflux for 24 hours
  5. temperatureAfter the mixture had been cooled
  6. extractionit was extracted with chloroform
  7. washThe extract was washed with 5% strength hydrochloric acid
  8. customdried
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0bcc7aea091e4a83829f19bafffdda90
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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