Lithium Hexamethyldisilazide → 4-(4-(3,3-Diphenyl-2-propenyl)-1-piperazinyl)benzenecarboximidamide

HRID 731545

Reaction equation

HRID 731545 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-:35][Si](C)(C)C)(C)C>O1CCCC1>[C:24]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20](=[NH:35])[NH2:21])=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 591866114-(4-(3,3-Diphenyl-2-propenyl)-1-piperazinyl)benzonitrile

Product 1

HCID 591866074-(4-(3,3-Diphenyl-2-propenyl)-1-piperazinyl)benzenecarboximidamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 12A (0.515 g, 1.36 mmol) in dry tetrahydrofuran (6 mL) was treated dropwise with LiHMDS (1M, 6.8 mL, 6.8 mmol), stirred for 16 hours, quenched with 1N HCl (8 mL), and filtered. The filter cake was collected to provide the desired product (0.45 g, 71%) that was used without further purification. MS (CI) m/e 397 (M+H)+.

Workup

  1. customquenched with 1N HCl (8 mL)
  2. filtrationfiltered
  3. customThe filter cake was collected

Sources & evidence

ORD record
ord-f615de3334bf4e5d8dc073a1350c2764
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Linked notes

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