Dimethylformamide → (+/-)-N-[3-[2-[2-(dibenzofuran-3-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Hydrochloride

HRID 635414Notes

Reaction equation

HRID 635414 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([O:14][CH2:15][CH2:16][NH2:17])[CH:2]=1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:23]=1)=[O:21].CN(C)C=O.[ClH:38].C(O)C>CO.C(Cl)(Cl)Cl>[ClH:38].[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([O:14][CH2:15][CH2:16][NH:17][CH2:19][CH:20]([C:22]2[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=2)[OH:21])[CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11346858N-[3-(2-bromoacetyl)phenyl]methanesulfonamideHCID 186152312-(Dibenzo[b,d]furan-3-yloxy)ethanamineHCID 21887872Ethanol hydrochloride

Product 1

HCID 18615217(+/-)-N-[3-[2-[2-(dibenzofuran-3-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following the procedures of Example 7, the above-identified compound was synthesized from 224.6 mg of Intermediate 5 and 170 mg of Intermediate 14, with the proviso that the following modification was incorporated. Thus, addition of dimethylformamide was omitted and the purification of the crude product was effected twice by a chromatography (methanol/chloroform of 1/20-1/10). The free amine compound (98.4 mg) was converted into its hydrochloride salt (the above-identified compound) with 1.1 eq. of 0.1 N hydrogenchloride/ethanol, whereupon the solvent was evaporated off under a reduced pressure. To the resulting residue was added diethyl ether and the deposited precipitate was washed diethyl ether and dried under a reduced pressure at 46° C., whereby the above-identified compound was obtained as a powdery product. Rf=0.27 (methanol/chloroform of 1/10).

Workup

  1. customthe purification of the crude product
  2. customwhereupon the solvent was evaporated off under a reduced pressure
  3. additionTo the resulting residue was added diethyl ether
  4. washthe deposited precipitate was washed diethyl ether
  5. customdried under a reduced pressure at 46° C.
  6. customwhereby the above-identified compound was obtained as a powdery product

Sources & evidence

ORD record
ord-4b1a35ad2cff4e5f8b5c8acc8ce73ad9
Source dataset
uspto-grants-2001_02
Patent number
US06187809B1

Reaction notes

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