Hydrochloric Acid → HCID 19791265, compound

HRID 1655194Notes

Reaction equation

HRID 1655194 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl.[N:26]([O-])=[O:27].[Na+]>O.C(OCC)C.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([N:26]=[O:27])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 99740131-[2-[Bis(4-fluorophenyl)methoxy]ethyl]piperazineHCID 23668193Sodium Nitrite

Product 1

HCID 19791265HCID 19791265, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-[2-[bis(4-fluorophenyl)-methoxy]ethyl]piperazine (1 g) in 1N-hydrochloric acid (3 ml) was added 1N-hydrochloric acid in order to adjust pH to 4. The mixture was stirred at 70°-75° C. and therein a solution of sodium nitrite (0.31 g) in water (0.5 ml) was added dropwise. The mixture was stirred at 70°-75° C. for one hour, cooled, and diluted with a mixture of diethyl ether and aqueous sodium bicarbonate solution. The organic layer was washed withbrine, dried, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluted with chloroform to yield 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-nitrosopiperazine (0.9 g) as an oil.

Workup

  1. stirringThe mixture was stirred at 70°-75° C. for one hour
  2. temperaturecooled
  3. washThe organic layer was washed withbrine,
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-5e18d197f10542e69a85662a383fbcb3
Source dataset
uspto-grants-1993_10
Patent number
US05250528

Reaction notes

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