4-Toluenesulfonyl chloride → HCID 19803495, compound

HRID 1682006Notes

Reaction equation

HRID 1682006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19803671HCID 19803671, compound

Product 1

HCID 19803495HCID 19803495, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1.3 g (0.005 mol) of N-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-hydroxymethyl-pyrrolidine are dissolved in 10 ml of pyridine, 1.05 g (0 0055 mol) of p-toluenesulphonic acid chloride are added and the mixture is stirred for 6 hours at ambient temperature. The excess pyridine is then distilled off in vacuo, the residue obtained is dissolved in methylene chloride and the organic phase is extracted with ice water. After the organic phase has been dried over magnesium sulphate it is concentrated by evaporation in vacuo. Yield: 1.4 g (66.7% of theory), Rf value: 0.40 (aluminium oxide, neutral, eluant: 2% ethanol in methylene chloride).

Workup

  1. distillationThe excess pyridine is then distilled off in vacuo
  2. customthe residue obtained
  3. extractionthe organic phase is extracted with ice water
  4. dry with materialAfter the organic phase has been dried over magnesium sulphate it
  5. concentrationis concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-f3af87071a5f401999d9a7f9a71062a6
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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