N,N-Dimethylallylamine → 1,5-Di(tert-butyl)-3-(N,N-dimethylaminopropyl)-1,1,3,5,5-Pentamethyltrisiloxane

HRID 2384128Notes

Reaction equation

HRID 2384128 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][SiH:7]([CH3:16])[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20]([CH2:22][CH:23]=[CH2:24])[CH3:21]>>[C:1]([Si:5]([CH3:17])([CH3:18])[O:6][Si:7]([CH2:24][CH2:23][CH2:22][N:20]([CH3:21])[CH3:19])([CH3:16])[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 75082N,N-DimethylallylamineHCID 589394291,5-Di(tert-butyl)-1,1,3,5,5-Pentamethyltrisiloxane

Product 1

HCID 577725601,5-Di(tert-butyl)-3-(N,N-dimethylaminopropyl)-1,1,3,5,5-Pentamethyltrisiloxane

Conditions

Temperature
90 °C

Procedure

1,5-Di(tert-butyl)-1,1,3,5,5-Pentamethyltrisiloxane and Karstedt's catalyst (30 ppm) were charged to a 100 mL Schlenk flask. The mixture was heated to 90° C. and N,N-dimethyl allyl amine (4.48 g) was added dropwise via syringe over 5 minutes. After complete addition, the reaction temperature was maintained at 90° C. for 3 hrs and the reaction was monitored by 1HNMR spectroscopy. Upon reaction completion, the volatiles were removed at 100° C./0.1 mmHg, and 15.2 g light yellow oil product was obtained.

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction temperature was maintained at 90° C. for 3 hrs
  3. customUpon reaction completion
  4. customthe volatiles were removed at 100° C./0.1 mmHg, and 15.2 g light yellow oil product
  5. customwas obtained

Sources & evidence

ORD record
ord-83b2975b35ec45e5b700556a25499c5c
Source dataset
uspto-grants-2012_09
Patent number
US08263669B2

Reaction notes

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