Triethylamine → 2,10-dimethyl-6-(1,2,2,6,6-pentamethylpiperidin-4-ylamino)-4,8-di-tert-butyl-12H-dibenzo-[d,g][1,3,2]dioxaphosphocine

HRID 1379225Notes

Reaction equation

HRID 1379225 reaction equation
[CH3:1][C:2]1[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[O:6][P:7](Cl)[O:8][C:9]3[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][C:13]([CH3:20])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1.C(N(CC)CC)C.[NH2:35][CH:36]1[CH2:41][C:40]([CH3:43])([CH3:42])[N:39]([CH3:44])[C:38]([CH3:46])([CH3:45])[CH2:37]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2[O:6][P:7]([NH:35][CH:36]3[CH2:37][C:38]([CH3:45])([CH3:46])[N:39]([CH3:44])[C:40]([CH3:43])([CH3:42])[CH2:41]3)[O:8][C:9]3[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][C:13]([CH3:20])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27845382,10-dimethyl-4,8-di-tert-butyl-6-chloro-12H-dibenzo[d,g][1,3,2]-dioxaphosphocine

Product 1

HCID 229099182,10-dimethyl-6-(1,2,2,6,6-pentamethylpiperidin-4-ylamino)-4,8-di-tert-butyl-12H-dibenzo-[d,g][1,3,2]dioxaphosphocineYield 57.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

10.12 g (25.0 mmol) of 2,10-dimethyl-4,8-di-tert-butyl-6-chloro-12H-dibenzo[d,g][1,3,2]-dioxaphosphocine [GB-A-2 250 990, Example 1a, page 17], 10.5 ml (75.0 mmol) of triethylamine and 100 ml of toluene are charged at room temperature and under nitrogen to a 350 ml sulfonation flask. With stirring, a solution of 4.26 g (25.0 mmol) of 4-amino-1,2,2,6,6-pentamethylpiperidine [Beilstein EII, Vol. 22, page 321 (1953)] in 30 ml of toluene is added dropwise to this suspension. The reaction mixture is refiuxed for 2 hours, then cooled to room temperature and filtered. The filtrate is concentrated on a vacuum rotary evaporator. Crystallisation of the residue from hexane yields 7.7 g (57%) of 2,10-dimethyl-6-(1,2,2,6,6-pentamethylpiperidin-4-ylamino)-4,8-di-tert-butyl-12H-dibenzo-[d,g][1,3,2]dioxaphosphocine (57%) (compound (101)) as a white powder, m.p. 207°-216° C. Analysis: calcd: C 73.57%; H 9.54%; N 5.19%; found: C 74.38%; H 10.03%; N 4.68%.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated on a vacuum rotary evaporator
  3. customCrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-63dd67b79e9d4bd5bf81208004e76199
Source dataset
uspto-grants-1997_09
Patent number
US05670642

Reaction notes

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