Triethylsilane → 2-(Trifluoromethyl)piperazine

HRID 1368161Notes

Reaction equation

HRID 1368161 reaction equation
[SiH](CC)(CC)CC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH:22]1[C:34]([F:37])([F:36])[F:35])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(C(F)(F)F)=O.CC(O)=O>[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:23][CH:22]1[C:34]([F:36])([F:37])[F:35])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[F:35][C:34]([F:37])([F:36])[CH:22]1[CH2:23][NH:24][CH2:25][CH2:26][NH:21]1

Participants

7

Reactant 3

HCID 12052TriethylsilaneHCID 18519781Dibenzyl-2-trifluoromethylpiperazineHCID 21226445Aluminium lithium hydride

Product 2

HCID 185197252-(Trifluoromethyl)piperazineHCID 18519781Dibenzyl-2-trifluoromethylpiperazine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-Trifluoromethylpiperazine (Jenneskens et al., Ref. 31c) was prepared through a four step route (Scheme 32). Using Lewis acid TiCl4, N,N′-dibenzylethylenediamine 54 reacted with trifluoropyruvates to afford hemiacetal 55, which was reduced at room temperature by Et3SiH in CF3COOH to lactam 56. LiAlH4 treatment then reduced lactam 56 to 1,4-dibenzyl-2-trifluoromethylpiperazine 57. Finally, hydrogenation of compound 57 in HOAc gave the desired product 2-trifluoromethylpiperazine 58.

Sources & evidence

ORD record
ord-3c98bb43e3b3420a9ed49d10e1d87688
Source dataset
uspto-grants-2003_06
Patent number
US06573262B2

Reaction notes

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