Methanesulfonic Acid → 8-Fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-ol

HRID 372172Notes

Reaction equation

HRID 372172 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][C@@H:7](N3CCNCC3)[C:6]=2[CH:23]=1.CS(O)(=O)=[O:26]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][CH:7]([OH:26])[C:6]=2[CH:23]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 54274820(R)-1-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine

Product 1

HCID 122755428-Fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-ol

Procedure

2.3 G. of enriched (R)-1-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine [αD = -25.0° (chloroform; c = 2.50%)] are heated to reflux with stirring for 24 hours in 0.57-M methanesulfonic acid and worked up in a manner analogous to that described in Example 13. For purification, the benzene extract is chromatographed on silica gel (0.2-0.5 mm) with chloroform. The eluted oily racemic 8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-ol melts at 90.5° C. after recrystallization from n-hexane.

Workup

  1. temperatureto reflux
  2. customFor purification
  3. extractionthe benzene extract
  4. customis chromatographed on silica gel (0.2-0.5 mm) with chloroform
  5. customThe eluted oily racemic 8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-ol melts at 90.5° C. after recrystallization from n-hexane

Sources & evidence

ORD record
ord-8fdfe61f2a2344a1a04dd3af7ad4c19b
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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