Piperidine, 1-(2-chloroethyl)-, hydrochloride → HCID 21269554, compound

HRID 1194326Notes

Reaction equation

HRID 1194326 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[S:9])[NH:8][C:4]=2[CH:3]=1.[ClH:12].[N:13]1([CH2:19][CH2:20][Cl:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])O.[Na+]>CO>[ClH:21].[ClH:12].[N:13]1([CH2:19][CH2:20][S:9][C:7]2[NH:8][C:4]3[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=3[N:6]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 516892Sodium BicarbonateHCID 7123736-Methyl-1H-benzimidazole-2-thiol

Product 1

HCID 21269554HCID 21269554, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.87 g (30 mmoles) of 5-methyl-benzimidazoline-2-thione, 6.54 g (35.5 mmoles) of 2-(1-piperidyl)-ethylchloride hydrochloride, 2.78 g (33 mmoles) of sodium hydrogencarbonate are dissolvent in 60 ml of methanol and the mixture is refluxed for 6 hours. The inorganic salt is filtered off, the filtrate is evaporated, and the title compound is precipitated by adding ethyl acetate and hydrochloric ethyl acetate. Weight: 9.32 g (90%). Melting point: 229°-230° C., which does not change after recrystallization from ethanol.

Workup

  1. temperaturethe mixture is refluxed for 6 hours
  2. filtrationThe inorganic salt is filtered off
  3. customthe filtrate is evaporated
  4. customthe title compound is precipitated
  5. additionby adding ethyl acetate and hydrochloric ethyl acetate
  6. customafter recrystallization from ethanol

Sources & evidence

ORD record
ord-21e68fd5fa384afca18e68283c69832b
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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