Water → N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1-piperidineethanamine

HRID 2419561Notes

Reaction equation

HRID 2419561 reaction equation
[I-].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N+:10](C)[C:11]3[CH:16]=CC=CC=3)[S:9][C:5]=2[CH:4]=1.NCC[N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N:10][CH2:11][CH2:16][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[S:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 33944N-(2-Aminoethyl)piperidineHCID 203138445-Chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide

Product 1

HCID 20313855N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1-piperidineethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (8.39g), N-(2-aminoethyl)piperidine (2.56g) and anhydrous sodium carbonate (1.06g) in 200 ml of anhydrous dimethylformamide is heated at 120° C under a nitrogen atmosphere for three hours. The reaction mixture is poured into 1000 ml of water and extracted with three 300 ml portions of dichloromethane. The combined organic extracts are washed with two 500 ml portions of water, dried over anhydrous sodium sulfate, and concentrated in vacuo to yield an oil. This oil is chromatographed on silica gel (1000 ml) eluting with (1) pentane (1000 ml), (2) chloroform (1000 ml), and finally methanol/chloroform (1:4, 2000 ml). The solid product from elution (3) is recrystallized from pentane to yield 4g of the title compound, melting point 42-44° C.

Workup

  1. extractionextracted with three 300 ml portions of dichloromethane
  2. washThe combined organic extracts are washed with two 500 ml portions of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield an oil
  6. customThis oil is chromatographed on silica gel (1000 ml)
  7. washeluting with (1) pentane (1000 ml), (2) chloroform (1000 ml), and finally methanol/chloroform (1:4, 2000 ml)
  8. washThe solid product from elution (3)
  9. customis recrystallized from pentane

Sources & evidence

ORD record
ord-4956deb3626c4de9a9c3ca65680a5657
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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