Triethylamine → HCID 68812043, compound

HRID 2100680Notes

Reaction equation

HRID 2100680 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:15]=2[CH2:22][CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(N(CC)CC)C.CCOC(C)=O.CCCCCC>Br>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[CH2:22][CH3:23])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 21226206Ethyl acetate hexaneHCID 68815759HCID 68815759, compound

Product 1

HCID 68812043HCID 68812043, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

4-(2-Ethyl-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester is refluxed in 48% HBr for 2 hours. After concentration, the residue is dissolved in DCM and (Boc)2O (1.5 eq) and triethylamine (4 eq) are added. The resulting mixture is stirred at room temperature for 30 minutes. After aqueous workup, flash column chromatography (30% EtOAc/hexane) gave 4-(2-Ethyl-4-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. MS: (ES+): 307.2 (M+1)+.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue is dissolved in DCM

Sources & evidence

ORD record
ord-fe3935359edf48d8b726f529c0313c4f
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

Loading…