Tert-Butylamine → HCID 71089303, compound

HRID 2273384Notes

Reaction equation

HRID 2273384 reaction equation
CC1C2=CC3[C:9](CCCCCCCCCCCCCC)([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]CCC)[C:10]4C(C=3C=C2CC=1)=CC=C[CH:11]=4.[CH2:46]([Li])[CH2:47][CH2:48][CH3:49].[C:51](N)(C)(C)[CH3:52].[C:56]([NH:60][Si:61]([CH:64]1[C:79]2[C:67](=[CH:68][C:69]3[C:70]([CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101]CCCCCC)(CCCCCCCCCCCCCC)[C:71]4[C:76]([C:77]=3[CH:78]=2)=[CH:75][CH:74]=[CH:73][CH:72]=4)[CH:66]=[C:65]1[CH3:108])([CH3:63])[CH3:62])([CH3:59])([CH3:58])[CH3:57]>C(OCC)C>[C:56]([NH:60][Si:61]([CH:64]1[C:79]2=[CH:78][C:77]3[C:76]([CH2:75][CH2:74][CH2:73][CH2:72][CH2:71][CH2:70][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH3:101])([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:9][CH2:10][CH3:11])[C:46]4[C:52]([C:69]=3[CH:68]=[C:67]2[CH:66]=[C:65]1[CH3:108])=[CH:51][CH:49]=[CH:48][CH:47]=4)([CH3:63])[CH3:62])([CH3:58])([CH3:57])[CH3:59]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 71089355HCID 71089355, compoundHCID 131732209HCID 131732209, compoundHCID 178418339Butyllithium

Product 1

HCID 71089303HCID 71089303, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 250 mL round flask, 2 methyl-9,9-ditetradecyl-3,9-dihydrocyclopenta[b]fluorene (4.9 g, 8.0 mmol) was dissolved in 100 mL of anhydrous diethyl ether, and then the temperature was lowered to −78° C. Then, n-butyllithium (1.6M hexane solution, 5.5 mL) was slowly injected thereto, followed by stirring at room temperature for 12 hours. After volatile materials were removed by vacuum, 100 mL of n-hexane was added to the mixture to lower the reactor temperature to −78° C., followed by addition of dichlorodimethylsilane (2.9 g). The temperature was again raised to room temperature, followed by stirring for 24 hours, and then salts were removed through filtering. Then, volatile materials were removed by vacuum. The product was again inputted to a 250 mL round flask, and dissolved in 100 mL of diethyl ether. The temperature was lowered to −78° C., and tert-butylamine (1.8 g, 24.1 mmol) was added thereto. The temperature was raised to room temperature, followed by stirring for 12 hours, and then volatile materials were completely removed by vacuum. Then, 200 mL of n-hexane was added to dissolve the resultant material, and salts were removed through filtering. The solvent was removed, to thereby obtain 5.5 g of a mixture of N-tert-butyl-1-(9,9-ditetradecyl-2-methyl-3,9-dihydrocyclopenta[b]fluoren-3-yl)-1,1-dimethylsilanamine and N-tert-butyl-1-(9,9-ditetradecyl-2-methyl-1,9-dihydrocyclopenta[b]fluoren-1-yl)-1,1-dimethylsilanamine (ratio=˜1:1), (yield: 92.7%), as high viscous material.

Workup

  1. customwas lowered to −78° C
  2. customAfter volatile materials were removed by vacuum, 100 mL of n-hexane
  3. additionwas added to the mixture
  4. customto −78° C.
  5. additionfollowed by addition of dichlorodimethylsilane (2.9 g)
  6. temperatureThe temperature was again raised to room temperature
  7. stirringby stirring for 24 hours
  8. customsalts were removed
  9. filtrationthrough filtering
  10. customThen, volatile materials were removed by vacuum
  11. customThe product was again inputted to a 250 mL round flask
  12. dissolutiondissolved in 100 mL of diethyl ether
  13. customwas lowered to −78° C.
  14. temperatureThe temperature was raised to room temperature
  15. stirringby stirring for 12 hours
  16. customvolatile materials were completely removed by vacuum
  17. additionThen, 200 mL of n-hexane was added
  18. dissolutionto dissolve the resultant material, and salts
  19. customwere removed
  20. filtrationthrough filtering
  21. customThe solvent was removed

Sources & evidence

ORD record
ord-9a322fa6a0b14366ba1de875a8712659
Source dataset
uspto-grants-2015_09
Patent number
US09120884B2

Reaction notes

Loading…