Triphenylphosphine → 3-(4-Phenylthiazol-2-yl)propan-1-amine

HRID 1397336Notes

Reaction equation

HRID 1397336 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][CH2:24][CH2:25][C:26]1[S:27][CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:30]=1)=[N+]=[N-]>C1COCC1.O>[C:31]1([C:29]2[N:30]=[C:26]([CH2:25][CH2:24][CH2:23][NH2:20])[S:27][CH:28]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 866775942-(3-Azidopropyl)-4-phenylthiazole

Product 1

HCID 242618563-(4-Phenylthiazol-2-yl)propan-1-amineYield 89.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Triphenylphosphine (485 mg, 1.85 mmol) was added to a solution of 2-(3-azidopropyl)-4-phenylthiazole (0.3 g, 1.23 mmol) in THF—H2O (10 mL, 8:2 v/v) at 0° C. The reaction mixture was allowed to warm up to room temperature, stirred for 8 h and then concentrated under reduced pressure. The residue was diluted with 1.5N HCl and the aqueous layer was washed with CH2Cl2. The pH of the aqueous layer was adjusted to ˜8-9 using 10% NaOH solution and the organic product was extracted with CH2Cl2. The combined extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 3-(4-phenylthiazol-2-yl)propan-1-amine (240 mg, yield 89%) as a pale yellow liquid, which was carried through without further purification. MS (ESI) m/z: Calculated for C12H14N2S: 218.09. found: 219.2 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with 1.5N HCl
  3. washthe aqueous layer was washed with CH2Cl2
  4. extractionthe organic product was extracted with CH2Cl2
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-22b35684d75949438568027d46e64e6a
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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