Formaldehyde → 1,1-Dimethylethyl 2,2-dimethyl-4-({1-[4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-1-piperazinecarboxylate

HRID 517705Notes

Reaction equation

HRID 517705 reaction equation
[CH2:1]=O.[CH3:3][C:4]1([CH3:17])[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:25]=[CH:24][C:23]([N+:26]#[C-:27])=[CH:22][CH:21]=1.C[Si]([N:34]=[N+:35]=[N-:36])(C)C>CO>[CH3:3][C:4]1([CH3:17])[CH2:9][N:8]([CH2:1][C:27]2[N:26]([C:23]3[CH:22]=[CH:21][C:20]([C:19]([F:28])([F:29])[F:18])=[CH:25][CH:24]=3)[N:36]=[N:35][N:34]=2)[CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 78378AzidotrimethylsilaneHCID 27594124-(Trifluoromethyl)phenyl isocyanideHCID 299224001,1-Dimethylethyl 2,2-dimethyl-1-piperazinecarboxylate

Product 1

HCID 680745071,1-Dimethylethyl 2,2-dimethyl-4-({1-[4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of formaldehyde (0.044 mL, 0.584 mmol) in methanol (2 mL) was added 1,1-dimethylethyl 2,2-dimethyl-1-piperazinecarboxylate (125 mg, 0.584 mmol, commercially available, for example from ChemPacific Corp., Baltimore, USA). The reaction mixture was stirred at room temperature for 1 hour before the addition of 4-(trifluoromethyl)phenylisocyanide (100 mg, 0.584 mmol, Fluorochem, Old Glossop, UK) and trimethylsilyl azide (0.092 mL, 0.701 mmol). The resulting reaction mixture was stirred at room overnight.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-5ddbe548ed5448e39e250f8764c6066a
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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