Triphenylphosphine → 1-(5-chlorothien-2-yl)ethanamine

HRID 2261995Notes

Reaction equation

HRID 2261995 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]([N:9]=[N+]=[N-])[CH3:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Cl:1][C:2]1[S:6][C:5]([CH:7]([NH2:9])[CH3:8])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86083512HCID 86083512, compound

Product 1

HCID 43769961-(5-chlorothien-2-yl)ethanamineYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(5-chloro-2-thienyl)ethyl azide (991 mg, 5.3 mmol) and triphenylphosphine (1.4 g, 5.3 mmol) in THF (10 mL) and water (0.4 mL) was heated to 60° C. for 1 h. After cooling to rt, the solution was concentrated in vacuo. The resulting residue was purified by flash chromatography (90% DCM: 10% methanol) to provide the desired 1-(5-chloro-2-thienyl)ethanamine (646 mg, 4.0 mmol, 75% yield) as a pink liquid. 1H NMR (400 MHz, CDCl3): 6.71 (d, 1H), 6.64 (d, 1H), 4.26 (q, 1H), 1.64 (br s, 2H), 1.44 (d, 3H).

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe solution was concentrated in vacuo
  3. customThe resulting residue was purified by flash chromatography (90% DCM: 10% methanol)

Sources & evidence

ORD record
ord-aeb7edee274c4069aba07bef835123a2
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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