Sodium Hydroxide → HCID 21449869, compound

HRID 596444Notes

Reaction equation

HRID 596444 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:4]=2[CH2:3]1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[OH-].[Na+]>>[F:13][C:10]1[CH:11]=[CH:12][C:7]2[S:6][C:5]3[CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=[CH:17][C:4]=3[CH2:3][CH:2]([N:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[C:8]=2[CH:9]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 21416136HCID 21416136, compound

Product 1

HCID 21449869HCID 21449869, compound

Procedure

9 G. of 10-chloro-8-fluoro-10,11-dihydro-3-trifluoromethyldibenzo[b,f]thiepin are treated with 11 g. of N-methylpiperazine and stirred for 10 minutes at 105°-110° C. The cooled mixture is treated with 2N sodium hydroxide and extracted with ether. The ether solution is washed neutral with water and shaken with dilute methanesulfonic acid. The acidic solution is made alkaline with sodium hydroxide and extracted with ether. The organic phase is washed with water, dried over magnesium sulfate and evaporated in a vacuum, and there is obtained 1-{8-fluoro-10,11-dihydro-3-trifluoromethyl-dibenzo[b,f]thiepin-10-yl]-4-methylpiperazine as a yellow oil which is converted into the methanesulfonate having a melting point of 224°-226° C. by treatment with methanesulfonic acid.

Workup

  1. extractionextracted with ether
  2. washThe ether solution is washed neutral with water
  3. extractionextracted with ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in a vacuum

Sources & evidence

ORD record
ord-a3ad8eb178ca49b1bc19654272f7b418
Source dataset
uspto-grants-1977_03
Patent number
US04011222

Reaction notes

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