Phenethylamine → HCID 66724543, compound

HRID 1818077Notes

Reaction equation

HRID 1818077 reaction equation
[F:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:11]([NH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[F:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:19][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 960892-Fluoronicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 66724543HCID 66724543, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-nicotinic acid (0.793 g, 5.59 mmol) and phenethylamine (0.705 mL, 5.59 mmol) were dissolved in acetonitrile (20 mL) containing triethylamine (1.56 mL, 11.2 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.97 g, 7.83 mmol) was added and the solution was allowed to stir for 16 hours. The reaction mixture was evaporated to dryness and purified by column chromatography on silica gel using a gradient of 0-40% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (0.196 g, 0.802 mmol, 14.3%). ESI-MS m/z calc. 244.1, found 245.2 (M+1)+. Retention time of 2.76 minutes.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by column chromatography on silica gel using a gradient of 0-40% ethyl acetate in hexanes
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b4b0004f1c9f4925b70fa191f1f0b222
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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