Tert-Butylamine → N-(1,1-Dimethylethyl)-1,1-dimethyl-1-(1,5,6,7-tetrahydro-3-phenyl-s-indacen-1-yl)silanamine

HRID 844415Notes

Reaction equation

HRID 844415 reaction equation
Cl[Si:2]([CH3:22])([CH3:21])[CH:3]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4]1.CCN(CC)CC.[C:30]([NH2:34])([CH3:33])([CH3:32])[CH3:31]>CCCCCC>[CH3:31][C:30]([NH:34][Si:2]([CH3:22])([CH3:21])[CH:3]1[C:14]2[C:6](=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4]1)([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 18628376Chlorodimethyl(1,5,6,7-tetrahydro-3-phenyl-s-indacen-1-yl)silane

Product 1

HCID 18628374N-(1,1-Dimethylethyl)-1,1-dimethyl-1-(1,5,6,7-tetrahydro-3-phenyl-s-indacen-1-yl)silanamineYield 88.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Chlorodimethyl(1,5,6,7-tetrahydro-3-phenyl-s-indacen-1-yl)silane (10.8277 g, 0.03322 moles) was stirred in hexane (150 mL) as NEt3 (3.5123 g, 0.03471 moles) and t-butylamine (2.6074 g, 0.03565 moles) were added. This mixture was allowed to stir for 24 hours. After the reaction period the mixture was filtered and the volatiles removed resulting in the isolation of the desired product as a thick red-yellow oil (10.6551 g, 88.7% yield). 1H NMR (CDCl3): d0.02 (s, 3 H), 0.04 (s, 3 H), 1.27 (s, 9 H), 2.16 (p, 3JHH=7.2 Hz, 2 H), 2.9-3.0 (m, 4 H), 3.68 (s, 1 H), 6.69 (s, 1 H), 7.3-7.5 (m, 4 H), 7.63 (d, 3JHH=7.4 Hz, 2 H). 13C NMR (CDCl3): d−0.32, −0.09, 26.28, 33.39, 34.11, 46.46, 47.54, 49.81, 115.80, 119.30, 126.92, 127.89, 128.46, 132.99, 137.30, 140.20, 140.81, 141.64, 142.08, 144.83.

Workup

  1. additionwere added
  2. customAfter the reaction period the mixture
  3. filtrationwas filtered
  4. customthe volatiles removed

Sources & evidence

ORD record
ord-efe4bdc714e9457f8294690839d92c11
Source dataset
uspto-grants-2002_04
Patent number
US06380294B1

Reaction notes

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