Acetone → 1-(2-Chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid hydrochloride

HRID 1732568Notes

Reaction equation

HRID 1732568 reaction equation
Cl.[Cl:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]([O:14]C)=[O:13])[CH2:7]1.CC(C)=O>Cl>[ClH:2].[Cl:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]([OH:14])=[O:13])[CH2:7]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 12769333Methyl 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride

Product 1

HCID 127693701-(2-Chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid hydrochlorideYield 186.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride (0.45 g.) in concentrated hydrochloric acid (10 ml.) was heated at 95°-100° C. for 2 hours, cooled and evaporated. The residue was evaporated several times with acetone and toluene to remove remaining traces of water. The solid obtained was stirred with acetone and then collected by filtration to give 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid hydrochloride (0.4 g.), m.p. 208°-210° C. (dec.).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was evaporated several times with acetone and toluene
  4. customto remove
  5. customThe solid obtained
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-59a7d37e3f3e47ed908a7c91e3692f74
Source dataset
uspto-grants-1980_12
Patent number
US04238488

Reaction notes

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