Ammonium Chloride → HCID 13207830, compound

HRID 434407Notes

Reaction equation

HRID 434407 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[F:13][C:14]1[CH:32]=[CH:31][C:17]2[C:18]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]3)=[N:19][O:20][C:16]=2[CH:15]=1.[Cl-].[NH4+]>BrC(Br)C.CCOCC.O1CCCC1>[F:13][C:14]1[CH:32]=[CH:31][C:17]2[C:18]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][C:27]([OH:30])([C:3]4[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=4)[CH2:28][CH2:29]3)=[N:19][O:20][C:16]=2[CH:15]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462224MagnesiumHCID 132078191-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone

Product 1

HCID 13207830HCID 13207830, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 112011,1-DibromoethaneCatalystHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.2 g of magnesium shavings and a few drops of dibromoethane in 30 ml of ether was added a solution of 10.3 g of 4-bromobenzotrifluoride in 20 ml of ether at such a rate so as to maintain reflux of the mixture. After the addition was complete, the mixture was diluted with 35 ml of tetrahydrofuran, and a solution of 6.3 g of 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone in 50 ml of tetrahydrofuran was slowly added. After one hr, the mixture was diluted with ether, poured into 400 ml of saturated ammonium chloride solution and extracted with ether. The organic extracts were washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate, filtered and concentrated. Trituration with hexane/ether gave 7 g (73%) of product, mp 150°-152° C. Recrystallization from ether gave the analytical sample, mp 152°-153° C.

Workup

  1. temperatureto maintain
  2. temperaturereflux of the mixture
  3. additionAfter the addition
  4. extractionextracted with ether
  5. washThe organic extracts were washed with water (2×), saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-634802dcb5ea47a4937d15a21a8f4233
Source dataset
uspto-grants-1983_08
Patent number
US04396770

Reaction notes

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