Hydrochloric Acid → HCID 19826904, compound

HRID 1086152Notes

Reaction equation

HRID 1086152 reaction equation
[ClH:1].[Br:2][C:3]1[S:4][C:5]([Br:19])=[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][NH:10][CH2:9][CH2:8][C:7]=12>C(O)C>[ClH:1].[Br:2][C:3]1[S:4][C:5]([Br:19])=[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][NH:10][CH2:9][CH2:8][C:7]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19826883HCID 19826883, compound

Product 1

HCID 19826904HCID 19826904, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperatureThe solution was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-169430b902ba4f9ab6fa937e458532e2
Source dataset
uspto-grants-1991_07
Patent number
US05028602

Reaction notes

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