Dimethylamine, hydrochloride → 3-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine

HRID 1649546Notes

Reaction equation

HRID 1649546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:10]=O)=[CH:4][CH:3]=1.Cl.[CH3:19][NH:20][CH3:21].[OH-].[Na+].C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH2:10][N:20]([CH3:21])[CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 543261733-(4-Chlorophenyl)-3-(3-pyridyl)-2-propenal

Product 1

HCID 542523273-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amineYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 0.25 g (1 mmol) crude 3-(4-chlorophenyl)-3-(3-pyridyl)-2-propenal, in a flask, was added in the following order: 0.73 g (9 mmol) dimethylamine hydrochloride, 10 ml methanol, 0.24 g (6 mmol) sodium hydroxide, 0.094 g (1.5 mmol) sodium cyanoborohydride and 5 g molecular sieves (3 Å). The mixture was stirred at room temperature under nitrogen for 3 days and then 100 ml methanol were added. After filtration the methanol was evaporated and the residue dissolved in a hydrochloric solution at pH 4.9 and washed with ether twice. The aqueous solution was made alkaline, extracted twice with ether and dried over MgSO4. Evaporation gave 0.18 g (66%) of pure title compound as an isomeric mixture having an approximate Z/E ratio of 54/46 (NMR).

Workup

  1. filtrationAfter filtration the methanol
  2. customwas evaporated
  3. dissolutionthe residue dissolved in a hydrochloric solution at pH 4.9
  4. washwashed with ether twice
  5. extractionextracted twice with ether
  6. dry with materialdried over MgSO4
  7. customEvaporation

Sources & evidence

ORD record
ord-30c035ef5b1b4449883e6924c9f205fa
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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