Dibenzyl-2-trifluoromethylpiperazine → 2-(Trifluoromethyl)piperazine

HRID 899350Notes

Reaction equation

HRID 899350 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH:15]1[C:27]([F:30])([F:29])[F:28])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC(O)=O>[CH2:20]([N:17]1[CH2:18][CH2:19][N:14]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:15]([C:27]([F:29])([F:30])[F:28])[CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[F:28][C:27]([F:30])([F:29])[CH:15]1[CH2:16][NH:17][CH2:18][CH2:19][NH:14]1

Participants

5

Reactant 2

HCID 18519781Dibenzyl-2-trifluoromethylpiperazineHCID 21226445Aluminium lithium hydride

Product 2

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Trifluoromethylpiperazine (Jenneskens et al., Ref. 88c) was prepared through a four step route (Scheme 56). Using Lewis acid TiCl4, N,N′-dibenzylethylenediamine reacted with trifluoropyruvates to afford the hemiacetal, which was reduced at room temperature by Et3SiH in TFA to afford the lactam. LiAlH4 treatment then reduced the lactam to 1,4-dibenzyl-2-trifluoromethylpiperazine. Finally, hydrogenation of the dibenzyl-2-trifluoromethylpiperazine in HOAc gave the desired product, 2-trifluoromethylpiperazine.

Sources & evidence

ORD record
ord-a9d41d4d04324ea6a6c8797f73ca6883
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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