Methanesulfonic Acid → HCID 19826883, compound

HRID 1086151Notes

Reaction equation

HRID 1086151 reaction equation
O[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([Br:12])[S:9][C:8]=1[Br:13].CS(O)(=O)=O>FC(F)(F)C(O)=O>[Br:13][C:8]1[S:9][C:10]([Br:12])=[C:11]2[CH:2]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:3][NH:4][CH2:5][CH2:6][C:7]=12

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 53821622HCID 53821622, compound

Product 1

HCID 19826883HCID 19826883, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(2-hydroxy-2-phenylethyl) 2,5-dibromothiophene-3-ethylamine (7.0 g) and methane sulphonic acid (1.57 ml) in trifluoroacetic acid (35 ml) was heated under reflux for 5 hours. The brown reaction mixture was evaporated and the residue suspended in iced water (70 ml), basified with 0.880 ammonia solution (7 ml) and extracted with dichloromethane (2×100 ml). The extracts were dried, filtered and evaporated to a dark brown oil. Chromatography on silica eluting with 2% methanol in dichloromethane gave 1,3-dibromo-4-phenyl-5,6,7,8-tetrahydro-4H-thieno[3,4-d]azepine. The crystal salt was prepared by addition of ethanolic hydrogen chloride (I equivalent) to an ethanol (15 ml) solution of the amine. The solution was cooled and filtered to give 1,3-dibromo-4-phenyl-5,6,7,8-tetrahydro-4H-thieno[3,4-d]azepine hydrochloride (m.p. 248°) as a tan solid. A second crop of product was obtained by diluting the mother liquors with diethyl ether.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe brown reaction mixture was evaporated
  3. extractionextracted with dichloromethane (2×100 ml)
  4. customThe extracts were dried
  5. filtrationfiltered
  6. customevaporated to a dark brown oil

Sources & evidence

ORD record
ord-91655235ab054c49b2ab448eeb4a257c
Source dataset
uspto-grants-1991_07
Patent number
US05028602

Reaction notes

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