Water → 3-(Thiophen-2-yl)propan-1-amine

HRID 1638758Notes

Reaction equation

HRID 1638758 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]#[N:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][NH2:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5664252-ThiophenepropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 408353-(Thiophen-2-yl)propan-1-amineYield 555.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The product of Example 41 (8.3 g, 10.5 mmol) dissolved in 25 ml of Et2O was added dropwise (15 min.) to a stirred slurry of lithium aluminium hydride (LAH) in 125 ml of dry Et2O under an Ar atmosphere at room temperature. After the addition was complete the reaction was stirred at room temperature an additional 18 h. With great care, 8.0 ml of water were added dropwise to the vigorously stirred reaction mixture. Following this, 8.0 ml of 4N NaOH were then carefully added. Finally 22 ml of H2O were added and the aluminum salts were filtered from the Et2O solution. The filtrate was concentrated to give 8.24 g of the title products which was used without further purification.

Workup

  1. additionAfter the addition
  2. additionwere then carefully added
  3. filtrationthe aluminum salts were filtered from the Et2O solution
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a3774f370dc2470787054ff6eca382a6
Source dataset
uspto-grants-1989_11
Patent number
US04880829

Reaction notes

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