Carbon Dioxide → Methyl-bis(2,2,6,6-tetramethylpiperidin-4-yl)amine

HRID 1955946ノート

反応式

HRID 1955946 の反応式
[CH2:1]1OC1.[CH3:4][C:5]1([CH3:24])[CH2:10][CH:9]([NH:11][CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)[CH2:8][C:7]([CH3:23])([CH3:22])[NH:6]1.CSC[C@H](NC(CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)C(O)=O.C=O.C(O)=O.C(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][N:11]([CH:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14]([CH3:21])([CH3:20])[CH2:13]1)[CH:9]1[CH2:10][C:5]([CH3:24])([CH3:4])[NH:6][C:7]([CH3:23])([CH3:22])[CH2:8]1

参加物

8

反応物 7

HCID 280Carbon DioxideHCID 284Formic AcidHCID 712FormaldehydeHCID 6354Ethylene OxideHCID 11430Potassium CarbonateHCID 128652N-(9H-Fluoren-9-ylacetyl)-S-methylcysteineHCID 5667082,2,6,6-Tetramethyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)-4-piperidinamine

生成物 1

HCID 19073312Methyl-bis(2,2,6,6-tetramethylpiperidin-4-yl)amine収率 49%

実験手順

) In accordance with the general procedure of Example 1b), the HALS diol (204) is prepared starting from 2-N-morpholino-4,6-bis[N-n-butyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazine (Example yl) with ethylene oxide; m.p. 114°-117° C. Analysis: calcd: C 65.84%; H 10.45%; N 16.60%. found: C 65.86%; H 10.33%; N 16.01%. ##STR61## δ) 1.) 40.48 g (0.14 mol) of bis(2,2,6,6-tetramethylpiperidin-4-yl)amine [EP-A-336 895, Ciba-Geigy] and 11.4 g (0.14 mol) of a 36% aqueous solution of formaldehyde are placed in a 200 ml sulfonation flask. Then 25.8 g (0.56 mol) of formic acid are added dropwise at room temperature. In the course of this addition the temperature in the reactor rises to 70° C., with evolution of CO2. The reaction mixture is then further stirred until it has cooled to room temperature. The aqueous phase is saturated with potassium carbonate and the reaction mixture is extracted 3 times with chloroform. The organic phases are combined, dried over potassium carbonate and concentrated on a vacuum rotary evaporator. Chromatography of the residue on silica gel with the solvent system hexane/dichloromethane 9:1+5% triethylamine yields 21 g (49%) of methyl-bis(2,2,6,6-tetramethylpiperidin-4-yl)amine, m.p. 51°-53° C., as a white powder. 1H-NMR (300 MHz, CDCl3):δ=2.25 ppm (s, 3H) methyl group at the nitrogen.

後処理

  1. additionIn the course of this addition the temperature in the reactor
  2. extractionthe reaction mixture is extracted 3 times with chloroform
  3. dry with materialdried over potassium carbonate
  4. concentrationconcentrated on a vacuum rotary evaporator

出典と根拠

ORDレコード
ord-f35b0c17fc284209be2012899ff27af5
出典データセット
uspto-grants-1998_07
特許番号
US05777008

反応ノート

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