Triethylsilane → 2-(Trifluoromethyl)piperazine

HRID 992348Notes

Reaction equation

HRID 992348 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 6). Using Lewis acid TiCl4, N,N′-dibenzylethylenediamine 11 reacted with trifluoropyruvates 12 to afford hemiacetal 13, which was reduced at room temperature by Et3SiH in CF3COOH to lactam 14. LiAlH4 treatment then reduced lactam 14 to 1,4-dibenzyl-2-trifluoromethylpiperazine 15. Finally, hydrogenation of compound 15 in HOAc gave the desired product 2-trifluoromethylpiperazine 16.

Sources & evidence

ORD record
ord-8483921fe6a7400d934f0b45e7313323
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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