Carbon Dioxide → HCID 67457963, compound

HRID 2368783Notes

Reaction equation

HRID 2368783 reaction equation
N#N.Br[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C@@H:9]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)[CH2:8][CH2:7]2.C([Li])CCC.[C:25](=[O:27])=[O:26]>C1COCC1>[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([C@@H:9]2[C:10]3[C:6](=[CH:5][C:4]([C:25]([OH:27])=[O:26])=[CH:12][CH:11]=3)[CH2:7][CH2:8]2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 947NitrogenHCID 67456730HCID 67456730, compoundHCID 178418339Butyllithium

Product 1

HCID 67457963HCID 67457963, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under the protection of N2, 1-((1S)-5-bromo-2,3-dihydro-1H-inden-1-yl)-4-methylpiperazine (660 g, 2.235 mol) and THF (3.3 L) were added to a 10 L three-neck flask, and the solution was stirred until dissolved. The system temperature was cooled to −78° C. in liquid nitrogen-acetone bath. n-butyllithium (n-BuLi) (2.5 M in hexane solution) (1072 mL, 2.682 mol, 1.2-fold) was added dropwise into the solution at −78° C.˜−82° C. After being stirred for 10 minutes, when the LC-MS assay shown that the reaction of the raw materials was completed, dry ice (170 g, 3.86 mol, 1.73-fold) was added carefully. The solution was then stirred for 10 minutes at −60° C.˜−75° C. After the reaction was completed, the cold bath was removed and aqueous solution of 2 N HCl was then added to adjust the pH value till pH=2. Most of the water was removed using rotary evaporator. The system was further dried overnight at 50° C.˜60° C. in a vacuum drying oven to obtain the title compound (1289 g, the actual product of 583 g providing 100% yield). This crude product was used in the next step of reaction directly.

Workup

  1. dissolutionuntil dissolved
  2. stirringAfter being stirred for 10 minutes
  3. stirringThe solution was then stirred for 10 minutes at −60° C.˜−75° C
  4. customthe cold bath was removed
  5. additionaqueous solution of 2 N HCl was then added
  6. customMost of the water was removed
  7. customevaporator
  8. customThe system was further dried overnight at 50° C.˜60° C. in a vacuum
  9. customdrying oven

Sources & evidence

ORD record
ord-e0e9ab2ef15a458e8e05cb0df4af18f7
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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