Methanol → tert-Butyl piperazine-1-carboxylate

HRID 2233278Notes

Reaction equation

HRID 2233278 reaction equation
C(C1C=CC([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=CC=1)#N.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C1(C)C=CC=CC=1>[C:15]([N:12]1[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2795512Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 143452tert-Butyl piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To t-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate (2.30 g, 8.0 mmol, prepared by reaction of the aryl-piperazine with Boc-anhydride) in toluene (20 ml) add DIBAH (diisobutylaluminum hydride) (1.0M in toluene, 12.8 ml, 12.8 mmol). Heat at 50° C. 1.5 h, allow to cool, add MeOH (10 ml) and water (10 ml). Filter and concentrate. Chromatograph the residue over silica to obtain the Boc-piperazine as a yellow solid.

Workup

  1. custom1.5 h
  2. temperatureto cool
  3. filtrationFilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-018d4f4457724c02a0b64ba4b47335d2
Source dataset
uspto-grants-2010_05
Patent number
US07709492B2

Reaction notes

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