Toluene → 4-(2-Pyridylmethyl)-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane

HRID 27875Notes

Reaction equation

HRID 27875 reaction equation
I[CH2:2][Si:3]([CH3:11])([CH3:10])[O:4][Si:5]([CH2:8]I)([CH3:7])[CH3:6].[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C1(C)C=CC=CC=1>O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:12]1[CH2:8][Si:5]([CH3:6])([CH3:7])[O:4][Si:3]([CH3:11])([CH3:10])[CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 195092-PyridinemethanamineHCID 2566811,3-Bis(iodomethyl)-1,1,3,3-tetramethyldisiloxane

Product 1

HCID 233402924-(2-Pyridylmethyl)-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 41.4 g. (0.1 mole) of 1,3-bis-iodomethyl-1,1,3,3-tetramethyl-disiloxane there is added dropwise with stirring 32.4 g. (0.3 mole) of 2-aminomethyl-pyridine while maintaining the temperature at 20° C. Stirring is continued at room temperature for 24 hours. The now heterogeneous mixture is combined with approximately 0.5 l. of toluene followed by approximately 0.5 l. of water. The equilibrated aqueous phase is then extracted with two 100 ml. portions of toluene. The combined organic phase is then washed twice with approximately 100 ml. of water to give 4-(2-pyridylmethyl)-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disilacyclohexane as the crude free base.

Workup

  1. stirringStirring
  2. extractionThe equilibrated aqueous phase is then extracted with two 100 ml
  3. washThe combined organic phase is then washed twice with approximately 100 ml

Sources & evidence

ORD record
ord-88eb27fe145143528c64dd0096180b8c
Source dataset
uspto-grants-1980_09
Patent number
US04224317

Reaction notes

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