Benzyl Bromide → HCID 178521611, compound

HRID 2356286Notes

Reaction equation

HRID 2356286 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:1]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 178511715HCID 178511715, compound

Product 1

HCID 178521611HCID 178521611, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of trans-4-aminocyclohexanol (7.90 g, 68.5 mmol) in acetonitrile (150 mL), was added cesium carbonate (51.4 g, 157.5 mmol) and benzyl bromide (18.2 g, 143.8 mmol). The solution was stirred at ambient temperature for 16 hours. The solution was complete by LC-MS and the mixture filtered through a frit, washed with additional acetonitrile, and condensed under reduced pressure. The solid was partitioned between water and dichloromethane (500 mL) and dried over sodium sulfate, filtered and solvent removed under reduced pressure to afford the title compound (17.14 g, 85%). ES-MS (m/z) 296.5 [M+1]+.

Workup

  1. filtrationthe mixture filtered through a frit
  2. washwashed with additional acetonitrile, and condensed under reduced pressure
  3. customThe solid was partitioned between water and dichloromethane (500 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-e3b7587c89b04712acda4382cd416dc1
Source dataset
uspto-grants-2010_07
Patent number
US07759342B2

Reaction notes

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