Hydrochloric Acid → HCID 66718642, compound

HRID 1430355Notes

Reaction equation

HRID 1430355 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[N:10]([O-])=O.[Na+].[CH3:14][C:15]1([CH3:24])[CH2:20][CH:19]([OH:21])[CH2:18][C:17]([CH3:23])([CH3:22])[NH:16]1>O.C(#N)C>[CH3:14][C:15]1([CH3:24])[CH2:20][CH:19]([OH:21])[CH2:18][C:17]([CH3:23])([CH3:22])[N:16]1[N:10]=[N:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 23668193Sodium Nitrite

Product 1

HCID 66718642HCID 66718642, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of concentrated HCl (30 ml, 32%) and water (30 ml) is charged into 100 ml three necked round bottomed flask followed by addition of p-Toluidine (10 g, 0.0.093 mol). The mixture is cooled to 0 to 5° C. and solution of sodium nitrite (11.2 g, 0.16 mol) in water (15 ml) is added into it while maintaining the temperature at 0 to 5° C. This reaction mixture is then slowly added into a solution of 2,2,6,6-tetramethyl-4-hydroxypiperidine (69 g, 0.44 mol) in acetonitrile (2000 ml) and the mixture is stirred at 0 to −5° C. for 1 h. The reaction mass is filtered and the mother liquor evaporated to dryness at 40° C. The solid residue is extracted with cyclohexane (500 ml) and diethyl ether (800 ml). The extracts are decolorized with charcoal (25 g) filtered through bed of celite and concentrated at 25 C to afford 6.0 g of 2,2,6,6-Tetramethyl-1-(p-tolyl-diazenyl)-piperidine-4-ol as a yellow solid, m.p. 85-86° C.

Workup

  1. temperaturewhile maintaining the temperature at 0 to 5° C
  2. filtrationThe reaction mass is filtered
  3. customthe mother liquor evaporated to dryness at 40° C
  4. extractionThe solid residue is extracted with cyclohexane (500 ml) and diethyl ether (800 ml)
  5. filtrationfiltered through bed of celite and
  6. concentrationconcentrated at 25 C

Sources & evidence

ORD record
ord-968e95de500b426e856a2cb617d61380
Source dataset
uspto-grants-2015_01
Patent number
US08940806B2

Reaction notes

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