Triphenylphosphine → (3-Phenylbenzo[b]thiophen-2-yl)methanamine

HRID 242860Notes

Reaction equation

HRID 242860 reaction equation
[N:1]([CH2:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[C:14]1([C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[S:9][C:5]=2[CH2:4][NH2:1])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 866688732-Azidomethyl-3-phenylbenzo[b]thiophene

Product 1

HCID 68157140(3-Phenylbenzo[b]thiophen-2-yl)methanamineYield 130.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-azidomethyl-3-phenylbenzo[b]thiophene (244 mg, 0.92 mmol) in THF (10 mL) was treated with a solution of triphenylphosphine (302 mg, 1.15 mmol) in water (1 mL) under a nitrogen atmosphere. The mixture was heated to 60° C. for 2 h and then cooled to RT. Volatile were removed under reduced pressure and the resulting residue was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording (3-phenylbenzo[b]thiophen-2-yl)methanamine (288 mg, quantitative). LCMS: RT 2.15 min [M-N3]+ 223.0

Workup

  1. temperaturecooled to RT
  2. customVolatile were removed under reduced pressure
  3. washwas washed with MeOH
  4. washthe product eluted with 2M NH3/MeOH
  5. additionThe product containing fractions
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5cddaa825454ba3a57f4a395cda0dd4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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