Tetrahydrofuran → HCID 13398989, compound

HRID 1906306Notes

Reaction equation

HRID 1906306 reaction equation
N1([C:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)CCCC1.[S:16](Cl)(=[O:19])(=[O:18])[NH2:17].C(N(CC)CC)C.[O:28]1CCCC1>>[O:28]=[C:15]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[S:16]([NH2:17])(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 888891-(3,4-Dihydro-2-naphthyl)pyrrolidine

Product 1

HCID 13398989HCID 13398989, compoundYield 74.6%

Procedure

A solution of 19.9 g (0.1 mol) of 2-pyrrolidino-3,4-dihydronaphthalene in 200 ml of tetrahydrofuran was treated, over a period of 1 hour, at -30° C., with a solution of 17.3 g (0.15 mol) of sulfamoyl chloride in 50 ml of tetrahydrofuran and then, at the same temperature, with a solution of 15.2 g (0.15 mol) of triethylamine in 50 ml of tetrahydrofuran, the mixture was brought to 20° C. within 3 hours and filtered, the filtrate was freed of solvent in vacuo and the residue was stirred with 200 ml of 2N HCl and 40 ml of CH2Cl2 for 24 hours. The solid obtained was recrystallized from isopropanol to give 16.9 g (74.6%) of a product of melting point 145°-146° C.

Workup

  1. filtrationfiltered
  2. customThe solid obtained
  3. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-40393ad7e30744bdb665c37c4ce2ba08
Source dataset
uspto-grants-1987_03
Patent number
US04650902

Reaction notes

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