Diisopropylethylamine → Tert-butyl 4-(1-(3-nitro-5-(trifluoromethyl)phenyl)ethyl)piperazine-1-carboxylate

HRID 2200143Notes

Reaction equation

HRID 2200143 reaction equation
CC1C=CC(S(O[CH:12]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([N+:24]([O-:26])=[O:25])[CH:15]=2)[CH3:13])(=O)=O)=CC=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(N(C(C)C)CC)(C)C>C1COCC1>[N+:24]([C:16]1[CH:15]=[C:14]([CH:12]([N:37]2[CH2:36][CH2:35][N:34]([C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH2:39][CH2:38]2)[CH3:13])[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 900212721-(3-Nitro-5-(trifluoromethyl)phenyl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 118223430Tert-butyl 4-(1-(3-nitro-5-(trifluoromethyl)phenyl)ethyl)piperazine-1-carboxylateYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir the mixture of 1-(3-nitro-5-(trifluoromethyl)phenyl)ethyl 4-methylbenzenesulfonate (350 mg, 0.90 mmol), 1-piperazinecarboxylic acid tert-butyl ester (335 mg, 1.8 mmol) and diisopropylethylamine (232 mg, 1.8 mmol) in THF (10 mL) for 12 hrs at 80° C. Concentrate the reaction mixture to obtain the crude product, purify by flash chromatography (silica gel, EtOAc:PE=1:10) to afford the title compound (280 mg, 77.1%). MS: (M+1): 404.2.

Workup

  1. concentrationConcentrate the reaction mixture
  2. customto obtain the crude product
  3. custompurify by flash chromatography (silica gel, EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-529e3e0985c147d8bcef89466f63883e
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…