Hydrazine hydrate (1:1) → 4-(Pyrrolidin-1-yl)butan-1-amine

HRID 1815442Notes

Reaction equation

HRID 1815442 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22500398HCID 22500398, compound

Product 1

HCID 27627624-(Pyrrolidin-1-yl)butan-1-amineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of the product from step c (4.32 g, 15.9 mmol) and hydrazine hydrate (3.85 ml, 79.4 mmol) in ethanol (75 ml) was heated at reflux for 1.5 h. The resultant white suspension was diluted with further ethanol (50 ml) and the solid removed by filtration. The filtrate was evaporated at reduced pressure and the residue was suspended in chloroform (50 ml). The solid was removed by filtration and the filtrate evaporated at reduced pressure to afford the title compound (1.91 g, 85%). 1H NMR 2.74-2.69 (2H, m), 2.52-2.42 (6H, m), 1.83-1.75 (4H, m), 1.64-1.46 (6H, m).

Workup

  1. temperatureat reflux for 1.5 h
  2. customthe solid removed by filtration
  3. customThe filtrate was evaporated at reduced pressure
  4. customThe solid was removed by filtration
  5. customthe filtrate evaporated at reduced pressure

Sources & evidence

ORD record
ord-dac5a886b65e4c4e89bb2f60135e167b
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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