Hydrochloric Acid → HCID 87132637, compound

HRID 1430356Notes

Reaction equation

HRID 1430356 reaction equation
Cl.[N+:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([O-:4])=[O:3].[N:12]([O-])=O.[Na+].F[B-](F)(F)F.[Na+].[CH3:22][C:23]1([CH3:32])[CH2:28][CH:27]([OH:29])[CH2:26][C:25]([CH3:31])([CH3:30])[NH:24]1>O.C(#N)C>[CH3:22][C:23]1([CH3:32])[CH2:28][CH:27]([OH:29])[CH2:26][C:25]([CH3:31])([CH3:30])[N:24]1[N:12]=[N:9][C:8]1[CH:10]=[CH:11][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 74754-NitroanilineHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 4343483Sodium TetrafluoroborateHCID 23668193Sodium Nitrite

Product 1

HCID 87132637HCID 87132637, compoundYield 4.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of concentrated HCl (15 ml, 32%) and water (15 ml) is charged into 100 ml three necked round bottomed flask followed by addition of 4-nitro-aniline (5 g, 0.04 mol). The mixture is cooled to 0 to 5° C. and solution of sodium nitrite (4.14 g, 0.06 mol) in water (5 ml) is added into it while maintaining temperature 0 to 5° C. This reaction mixture is then slowly added into a solution of sodium tetrafluoroborate (6.6 g, 0.06 mol) in water (60 ml) at 0 to 5° C. The resulting solution of diazonium tetrafluoroborate salt is then added to solution of 2,2,6,6-tetramethyl-4-hydroxypiperdine (25.1 g, 0.16 mol) in acetonitrile (1000 ml)) and the mixture is stirred at 0 to −5° C. for 1 h. This reaction mixture filtered and mother liquor is evaporated to dryness at 40° C. The residue is extracted with diethyl ether (200 ml) the extract is decolorized with charcoal (50 g), filtered through bed of celite and concentrated to dryness to afford 0.56 g of 2,2,6,6-Tetramethyl-1-(4-nitrophenyldiazenyl)-piperidin-4-ol as a yellow solid, m.p. 108-110° C.

Workup

  1. temperaturewhile maintaining temperature 0 to 5° C
  2. filtrationThis reaction mixture filtered
  3. custommother liquor is evaporated to dryness at 40° C
  4. extractionThe residue is extracted with diethyl ether (200 ml) the extract
  5. filtrationfiltered through bed of celite and
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f248639eff0c4e679ae25a27e52a7aca
Source dataset
uspto-grants-2015_01
Patent number
US08940806B2

Reaction notes

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