Hydrochloric Acid → Methyl 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride

HRID 1732567

Reaction equation

HRID 1732567 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Cl.Cl.[NH:18]1[CH2:23][CH2:22][CH:21]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH2:19]1.Cl>CO>[ClH:8].[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][N:18]1[CH2:23][CH2:22][CH:21]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 119062-Chlorobenzyl chlorideHCID 201540Norarecoline Hydrochloride

Product 1

HCID 12769333Methyl 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochlorideYield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (2.2 g.) and 2-chlorobenzyl chloride (1.63 g.) were added to a solution of methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (1.63 g.) in methanol (10 ml.). The solution obtained was kept for 24 hours at 20°-25° C. and then evaporated. Water (20 ml.) and 10% w/v sodium carbonate solution were then added to the residue to give a mixture of pH 10. This mixture was extracted with ether (2×20 ml.). The combined extracts were washed with water, dried (MgSO4) and evaporated. The residual oil was dissolved in acetone to give a solution which was treated with a slight excess of ethereal hydrogen chloride. The solid which precipitated was collected by filtration and washed with acetone to give methyl 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (1.5 g.) m.p. 171°-175° C.

Workup

  1. customThe solution obtained
  2. customevaporated
  3. additionwere then added to the residue
  4. customto give
  5. additiona mixture of pH 10
  6. extractionThis mixture was extracted with ether (2×20 ml.)
  7. washThe combined extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. dissolutionThe residual oil was dissolved in acetone
  11. customto give a solution which
  12. customThe solid which precipitated
  13. filtrationwas collected by filtration
  14. washwashed with acetone

Sources & evidence

ORD record
ord-ef6a323c0a934e0eb80c165241e4f9cc
Source dataset
uspto-grants-1980_12
Patent number
US04238488

Linked notes

Loading…