Phenethylamine → HCID 57884181, compound

HRID 1818082Notes

Reaction equation

HRID 1818082 reaction equation
F[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:11]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:27]([NH2:35])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH:11]1([O:16][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([NH:35][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:6])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 7298CyclopentanolHCID 960892-Fluoronicotinic acidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57884181HCID 57884181, compoundYield 1.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-nicotinic acid (84.7 mg, 0.600 mmol, cyclopentanol (51.6 mg, 0.600 mmol) and potassium bis(trimethylsilyl)amide (478 mg, 2.40 mmol) were combined in 0.6 mL of N,N-dimethylformamide and subjected to microwave irradiation for 3 minutes at 180° C. Phenethylamine (72.7 mg, 0.600 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (304 mg, 0.800 mmol) was added and the solution was allowed to stir for 16 hours. The mixture was then purified by reverse phase preparative liquid chromatography to yield the pure product (2.9 mg, 0.0093 mmol, 1.6%) ESI-MS m/z calc. 310.2, found 311.2 (M+1)+. Retention time of 3.40 minutes.

Workup

  1. customirradiation for 3 minutes at 180° C
  2. customThe mixture was then purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-bb03e016879949faa4a0dfb180d4f207
Source dataset
uspto-grants-2009_10
Patent number
US07598412B2

Reaction notes

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