Imidazole → HCID 53306515, compound

HRID 1050408Notes

Reaction equation

HRID 1050408 reaction equation
ClC1[CH:7]=[C:6](NC2N=CN=C(NC(C3CC3)=O)C=2)[C:5](=O)[N:4]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29](F)[CH:28]=3)(C)NC(=O)C=12.N1C=CN=C1.[Si:39](Cl)([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].[OH2:47]>ClCCl>[CH2:22]([NH:4][CH2:5][CH2:6][CH2:7][O:47][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 118598561HCID 118598561, compound

Product 1

HCID 53306515HCID 53306515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(benzylamino)propan-1-ol (1, 2.0 g, 12.1 mmol) in dichloromethane (20 mL), imidazole (2.47 g, 36.0 mmol) and tert-butyldimethylsilyl chloride (1.1 g, 13 mmol) were added at room temperature. The reaction mass was stirred at room temperature for 16 h. Water was added to the reaction mixture and layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated to afford N-benzyl-3-((tert-butyldimethylsilyl) oxy) propan-1-amine (2) as brown solid. Yield: 3.2 g, 94%; MS (ESI) m/z 280.29 [M−1]−.

Workup

  1. customwere separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a28bf9cfd8da49ec85f057277eae594d
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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