Isopropyl isocyanate → HCID 69410678, compound

HRID 1592751Notes

Reaction equation

HRID 1592751 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:21]([N:24]=[C:25]=[O:26])([CH3:23])[CH3:22]>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][C:25]([NH:24][CH:21]([CH3:23])[CH3:22])=[O:26])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanate3×HCID 2795530tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate

Product 1

HCID 69410678HCID 69410678, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-Boc-4-(2-aminophenyl)-piperazine (270 mg, 1.0 mmol) in 10 mL of THF was added isopropyl isocyanate (90 uL, 1.46 mmol). After stirring for about 1 hour, another 90 microliter of isopropyl isocyanate was added. After stirring for about 3 days, another 290 microliter of isopropyl isocyanate was added. After stirring overnight, the solution was concentrated. Purification by silica gel chromatography (35 g SiO2, 20 to 50% EtOAc/hexanes, over 30 minutes at 35 mL/min) afforded about 240 mg (0.66 mmol, 66%) of the title compound as a white solid. LRMS: 363.2 (M+1)

Workup

  1. stirringAfter stirring for about 3 days
  2. stirringAfter stirring overnight
  3. concentrationthe solution was concentrated
  4. customPurification by silica gel chromatography (35 g SiO2, 20 to 50% EtOAc/hexanes, over 30 minutes at 35 mL/min)

Sources & evidence

ORD record
ord-37d1fa2070a3411d9484e25fc1b26931
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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