Water → 1-(Cyclopropylmethyl)piperazine

HRID 1987552Notes

Reaction equation

HRID 1987552 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=O)[CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[CH:7]1([CH2:10][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20642351-(Cyclopropylcarbonyl)piperazineHCID 21226445Aluminium lithium hydride

Product 1

HCID 9658751-(Cyclopropylmethyl)piperazineYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (770 mg, 20.3 mmol) was suspended in tetrahydrofuran (150 mL), 1-(cyclopropylcarbonyl)piperazine (1.56 g, 10.1 mmol) was gradually added thereto, and the reaction mixture was heated under reflux for 30 minutes. The reaction mixture was cooled to room temperature, and 0.8 mL of water, 0.8 mL of a 15% aqueous solution of sodium hydroxide and 2.3 mL of water were sequentially gradually added thereto. The precipitated insoluble matter was removed by filtration through Celite, and the filtrate was evaporated to give the title compound (1.40 g) as a colorless oil. The product was used for the synthesis of (8E,12E,14E)-7-((4-cyclopropylmethylpiperazin-1-yl)carbonyl)oxy-3,6,16,21-tetrahydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (the compound of Example 27) without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customThe precipitated insoluble matter was removed by filtration through Celite
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-301e09e076484e07bb4db8b2bc351aa2
Source dataset
uspto-grants-2009_06
Patent number
US07550503B2

Reaction notes

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