Pyridine → HCID 18665738, compound

HRID 365464Notes

Reaction equation

HRID 365464 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][OH:16])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.N1C=CC=CC=1>CS(C)=O>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH:15]=[O:16])[CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 18665735HCID 18665735, compound

Product 1

HCID 18665738HCID 18665738, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-(2,2-Diphenylethyl)-3(S)-hydroxymethyl-piperidine (Example 18, Step B)-(2.10 g, 7.10 mmol) and Et3N (2.97 mL, 21.3 mmol) were dissolved in dry DMSO (40 mL) and cooled in an ice bath. Pyridine SO3 complex (3.39 g, 21.3 mmol) was added slowly, and the solution was stirred for 1 hr while allowing to warm to room temperature. The solution was poured into ice water, extracted with CH2CL2 (2×), the combined organics washed with satd NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration gave the title compound without further purification. Step B: Preparation of 1-(2,2-Diphenylethyl)-3(S)-[N-(1-(cyanobenzyl)-1H-imidazol-5-ylethyl)aminomethyl]-piperidine

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with CH2CL2 (2×)
  3. washthe combined organics washed with satd NaHCO3 solution, H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-738663d048aa40a483be42237a04aaf0
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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