Methanesulfonyl chloride → HCID 19741722, compound

HRID 2255082Notes

Reaction equation

HRID 2255082 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[C:6]1([CH:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:15][CH:14]=2)[CH2:4][CH2:3][N:2]([CH3:1])[CH3:20])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12874833HCID 12874833, compound

Product 1

HCID 19741722HCID 19741722, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5.25 g of N,N-dimethyl-γ-(4-aminophenoxy)benzenepropanamine in 30 ml of pyridine cooled to 10° C. by means of an external ice bath was treated with 1.86 ml of methanesulfonylchloride under a nitrogen atmosphere. The ice bath was removed and the reaction mixture stirred at room temperature overnight. The solution was poured into 30 ml of water, treated with acid and evaporated in vacuo. The residue was purified by high pressure liquid chromatography over silica gel eluting with methylene chloride/methanol/ammonium hydroxide (100:5:1). The appropriate fractions were combined and concentrated in vacuo providing 4.15 g of an oil which crystallized upon cooling. Recrystallization from ethanol provided 2.5 g of the desired title product as off-white crystals, m.p. 145°-147° C.

Workup

  1. customThe ice bath was removed
  2. additionThe solution was poured into 30 ml of water
  3. additiontreated with acid
  4. customevaporated in vacuo
  5. customThe residue was purified by high pressure liquid chromatography over silica gel eluting with methylene chloride/methanol/ammonium hydroxide (100:5:1)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-643716ac88f2475f800caf88ad9fbbcc
Source dataset
uspto-grants-1993_08
Patent number
US05238959

Reaction notes

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