Dimethylformamide → HCID 4780938, compound

HRID 1263249Notes

Reaction equation

HRID 1263249 reaction equation
Br.Br.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 20455110HCID 20455110, compound

Product 1

HCID 4780938HCID 4780938, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.6 parts of 1-(4-methoxyphenyl)piperazine dihydrobromide, 7.9 parts of 2-bromopyridine, 8.4 parts of potassium carbonate and 90 parts of N,N-dimethylformamide is stirred and refluxed overnight. The reaction mixture is diluted with water and the product is extracted twice with benzene. The combined extracts are dried, filtered and evaporated. The residue is crystallized from 1,1'-oxybisbutane. The product is filtered off and dried, yielding 8 parts (74%) of 1-(4-methoxyphenyl)-4-(2-pyridinyl)piperazine; mp. 125.6° C.

Workup

  1. temperaturerefluxed overnight
  2. extractionthe product is extracted twice with benzene
  3. customThe combined extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from 1,1'-oxybisbutane
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-1c33dcf1e880403bacbc659ce91a3955
Source dataset
uspto-grants-1984_06
Patent number
US04456605

Reaction notes

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