2-Fluoropyridine → HCID 19737302, compound

HRID 258314Notes

Reaction equation

HRID 258314 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]23[CH2:23][CH:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=42)[C:15]2[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.F[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.[F-].[K+]>CN1CCCC1=O>[CH:21]1[C:22]2[C:9]3([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=5)[CH2:3][CH2:4]4)[CH2:23][CH:16]([C:15]4[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 522689Potassium FluorideHCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 19737302HCID 19737302, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-piperidine (0.305 g, 1.0 mmol, prepared as described in Example 8b), 2-fluoropyridine (0.117 g, 1.2 mmol), and anhydrous potassium fluoride (0.174 g, 3.0 mmol) were heated to 150° C. in 3 mL N-methylpyrrolidinone for 52 hours. The warm reaction mixture was added slowly to a rapidly stirring mixture of aqueous NaOH/ice/methanol to give a tan precipitate. The solid was collected and washed with water. The solid was dissolved in methanolic hydrogen chloride and concentrated to dryness several times from methanol to give the hydrochloride salt of the title compound as a white solid (0.239 g, 0.5 mmol, 50%), mp 270° C. (decomp); MS(CI): 382 (M+H); NMR (300 MHz, DMSO-d6): 10.27(br s, 1H), 7.95-7.85(m, 2H), 7.39-7.33(m, 5H), 7.04-6.96(m, 5H), 6.85(br m, 1H), 4.47(s, 1H), 4.41(s, 2H), 4.20-4.00(br m, 1H), 3.66-3.30(m, 4H), 2.76(s, 2H), 2.20-2.04(m, 4H).

Workup

  1. customThe warm reaction mixture
  2. additionwas added slowly to
  3. customto give a tan precipitate
  4. customThe solid was collected
  5. washwashed with water
  6. dissolutionThe solid was dissolved in methanolic hydrogen chloride
  7. concentrationconcentrated to dryness several times from methanol

Sources & evidence

ORD record
ord-a99e563668214849b144b2cf0f0f5ae0
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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