p-Toluenesulfonic acid → HCID 18663628, compound

HRID 1956589Notes

Reaction equation

HRID 1956589 reaction equation
Br[CH2:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[CH3:18][NH:19][CH2:20][CH2:21][CH3:22].[S:23]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([O-:26])(=[O:25])=[O:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[S:23]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([OH:26])(=[O:25])=[O:24].[CH:17]1[C:5]2[CH:4]=[C:3]([CH2:2][N:19]([CH3:18])[CH2:20][CH2:21][CH3:22])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 12315N-MethylpropylamineHCID 85570p-ToluenesulfonateHCID 18663590HCID 18663590, compound

Product 1

HCID 18663628HCID 18663628, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Preparation analogous to Example 2 from 10-bromomethyl-dibenz[b,f]oxepine and N-methyl-N-propylamine. Tosylate prepared with 1 equivalent of p-toluenesulfonic acid in ethyl acetate, crystallised from dichloromethane/tert-butyl methyl ether. Yield: 68%; melting point: 179°-180° C.; 1H-NMR (CD3OD, 200 MHz): 0.97 (t, 3H); 1.78 (m, 2H); 2.36 (s, 3H); 3.15 (mbr, 2H); 4.50 (mbr, 2H); 7.17-7.75 (m, ca. 13H); MS: 279 (M+, free base), 250, 207.

Workup

  1. customcrystallised from dichloromethane/tert-butyl methyl ether

Sources & evidence

ORD record
ord-b04fa4ddc5a84578bac49096213b2a2f
Source dataset
uspto-grants-1998_07
Patent number
US05780501

Reaction notes

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