Aniline → HCID 66718671, compound

HRID 1430353Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]([O-])=O.[Na+].[CH3:12][C:13]1([CH3:22])[CH2:18][CH:17]([OH:19])[CH2:16][C:15]([CH3:21])([CH3:20])[NH:14]1.[OH-].[Na+]>O.Cl.ClCCl>[CH3:12][C:13]1([CH3:22])[CH2:18][CH:17]([OH:19])[CH2:16][C:15]([CH3:21])([CH3:20])[N:14]1[N:8]=[N:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

9.31 g Aniline is added to a mixture of 50 g ice and 29.4 ml aqueous HCl (32% w/w). Then, a solution of 6.90 g NaNO2 in 30 ml water is slowly added while keeping the temperature between −5 and 0° C. To this solution, a cold (−5° C.) solution of 15.7 g 2,2,6,6-tetramethyl-4-hydroxypiperidine in 30 ml water and 9.8 ml aqueous HCl (32% w/w) and a cold solution of 16 g NaOH in 40 ml water are slowly added sequentially while keeping the temperature in the range from −5 to 0° C. The thick brown suspension is allowed to warm up to 23° C. and is then diluted with 100 ml dichloromethane. The organic phase is separated, evaporated and chromatographed on silica gel with hexane-ethylacetate (2:1) to afford 17.4 g of 2,2,6,6-tetramethyl-1-phenyldiazenyl-piperidin-4-ol as a slightly yellow oil which solidifies on standing. A sample of this material is recrystallized from dichloromethane-hexane to afford light yellow solid, m.p. 68-70° C.

Workup

customthe temperature between −5 and 0° C
customfrom −5 to 0° C
customThe organic phase is separated
customevaporated
customchromatographed on silica gel with hexane-ethylacetate (2:1)

Sources & evidence

ORD record: ord-d2b83651c60448e0b5590c6fb3b00fac
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940806B2

Reaction notes

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