Triethylamine → HCID 68931842, compound

HRID 1926681Notes

Reaction equation

HRID 1926681 reaction equation
[CH:1]1([CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]2[CH2:10][CH2:9][NH:8][CH2:7][C@H:6]2C)[CH2:3][CH2:2]1.Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[CH2:31](N(CC)CC)C>CC#N>[CH:1]1([CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[CH:13]=2)[N:5]2[CH2:6][CH2:7][N:8]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:9]([CH3:31])[CH2:10]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 68931957HCID 68931957, compound

Product 1

HCID 68931842HCID 68931842, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of crude (2R)-1-(cyclopropyl(3-(trifluoromethyl)phenyl)methyl)-2-methylpiperazine (3.15 g, 105.6 mmol) in 25 mL of MeCN was added tert-butyl bromoacetate (2.046 ml, 12.67 mmol), followed by slow addition of triethylamine (2.203 ml, 15.837 mmol). The reaction mixture was stirred at rt overnight. The solution was evaporated to dryness and the residue was submitted to flash chromatography (SiO2, hexane to hexane/EtOAc=100:5 to 100:10 to 100:30) to give tert-butyl 2-((R)-4-(cyclopropyl(3-(trifluoromethyl)phenyl)methyl)-2-methylpiperazin-1-yl)acetate as a colorless oil.

Workup

  1. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-9c151826458e438b95f76fbe1dd92f7b
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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