Pyridine → HCID 21939791, compound

HRID 1242935Notes

Reaction equation

HRID 1242935 reaction equation
[N:1]1([CH2:6][C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([NH2:17])[CH:11]=[CH:10][C:9]=3[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=C[CH:19]=1.[C:24](Cl)(=O)[O:25]C1C=CC=CC=1.Cl.[F:35][C:36]1[CH:41]=[CH:40][C:39]([CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:38][CH:37]=1.[OH-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[F:35][C:36]1[CH:41]=[CH:40][C:39]([CH:42]2[CH2:43][CH2:44][N:45]([C:24]([NH:17][C:12]3[CH:11]=[CH:10][C:9]4[CH:8]=[C:7]([CH2:6][N:1]5[CH2:5][CH2:4][CH2:3][CH2:2][CH2:19]5)[CH2:16][CH2:15][C:14]=4[CH:13]=3)=[O:25])[CH2:46][CH2:47]2)=[CH:38][CH:37]=1

Participants

9

Reactant 5

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochlorideHCID 21939977HCID 21939977, compound

Product 1

HCID 21939791HCID 21939791, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(1-Pyrrolidinylmethyl)-7,8-dihydro-2-naphthalenamine obtained in Reference Example 54 (50 mg, 0.22 mmol) and pyridine (35 mg, 0.44 mmol) were dissolved in tetrahydrofuran (3 ml). Phenyl chlorocarbonate (38 mg, 0.24 mol) was added to the solution under ice-cooling, which was stirred for 10 minutes. The reaction mixture was concentrated, and dimethylsulfoxide (5 ml) was added to the residue. 4-(4-Fluorophenyl)piperidine hydrochloride (57 mg, 0.26 mmol) and 4N aqueous sodium hydroxide solution (0.066 ml, 0.26 mmol) were added to the reaction mixture at room temperature while stirring, which was stirred for 30 minutes. Ethyl acetate and water were added to the mixture, and extraction was conducted. The organic layer was washed with water, and concentrated. Diisopropyl ether was added to the residue. The crystallized product was collected by filtration, washed with diisopropyl ether, to give 4-(4-fluorophenyl)-N-[6-(1-piperidinylmethyl)-7,8-dihydro-2-naphthalenyl]-1-piperidinecarboxamide (48 mg) as a white powder.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additiondimethylsulfoxide (5 ml) was added to the residue
  4. stirringwhile stirring
  5. stirringwhich was stirred for 30 minutes
  6. washThe organic layer was washed with water
  7. concentrationconcentrated
  8. additionDiisopropyl ether was added to the residue
  9. filtrationThe crystallized product was collected by filtration
  10. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-d9da0803e8fb4b5892c77c5ac65edabb
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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