8-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline → tert-Butyl 4-(1,2,3,4-tetrahydroquinolin-8-yl)piperazine-1-carboxylate

HRID 1371514Notes

Reaction equation

HRID 1371514 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pt]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[NH:22][CH2:21][CH2:20][CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 155406788-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline

Product 1

HCID 21070955tert-Butyl 4-(1,2,3,4-tetrahydroquinolin-8-yl)piperazine-1-carboxylateYield 94.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

The compound of Step 2 (280 mg, 0.89 mmol) is dissolved in EtOH (70 mL), and Pt/C 10% (300 mg) is added. The mixture is pressurized to 45 psi under hydrogen and reacted for about 4 hours. The mixture is filtered over celite and concentrated. The residue is purified to afford about 266 mg of 8-(4-t-butyloxycarbonylpiperazin-1-yl)-1,2,3,4-tetrahydroquinoline (94%). EIS-MS 318.1 [M+1]

Workup

  1. customreacted for about 4 hours
  2. filtrationThe mixture is filtered over celite and
  3. concentrationconcentrated
  4. customThe residue is purified

Sources & evidence

ORD record
ord-ac3f519e8bfc47d78d906df483bba41c
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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