Sodium Bicarbonate → N-[4-[4-[ethyl(7-fluoroheptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide

HRID 1654315Notes

Reaction equation

HRID 1654315 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].C(=O)(O)[O-].[Na+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][F:33]>C(#N)C>[CH2:1]([N:3]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][F:33])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=1)[OH:8])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 30285061-Bromo-7-fluoroheptaneHCID 10779588N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

Product 1

HCID 10692503N-[4-[4-[ethyl(7-fluoroheptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Procedure B (Example 17, Step IV) a stirred mixture of N-[4-[4-(ethylamino)-1-hydroxybutyl]phenyl]methanesulfonamide (Example 7, Step II) and sodium bicarbonate in acetonitrile was allowed to react with 1-bromo-7-fluoroheptane (Step II) to give N-[4-[4-[ethyl(7-fluoroheptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide, a compound of Formula I'. A mixture of this compound and 0.5 equivalents of fumaric acid was crystallized from acetone to give the titled product, mp 137°-138° C. Anal. calc'd for C22H37N2O5S: C, 57.36; H, 8.10; N, 6.08; S, 6.96. Found: C, 57.34; H, 8.08; N, 6.03; S, 6.95.

Sources & evidence

ORD record
ord-88f9dc93e52242c6a3b5d161cb6e6794
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

Loading…