Benzyl Bromide → HCID 178525079, compound

HRID 2091659Notes

Reaction equation

HRID 2091659 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1>CC#N>[CH2:23]([N:1]([C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[O:9])[CH2:4][CH2:3]1)[CH2:23][C:20]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178511567HCID 178511567, compound

Product 1

HCID 178525079HCID 178525079, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

To an 80° C. heated mixture of trans-4-Aminocyclohexanecarboxylic acid (8 g, 55.97 mmol) and K2CO3 (23.4 g) in 112 mL of CH3CN, was added dropwise a solution of BnBr (23.3 mL, 195.5 mmol) in 70 mL of CH3CN by addition funnel. Reaction stirred overnight at 80° C. The reaction was cooled to room temperature and filtered. Precipitate did not form in filtrate like it did with the cis-somer so the filtrate was concentrated to an oil and carried on to next step (23.01 g, 99% yield).

Workup

  1. additionby addition funnel
  2. customReaction
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered
  5. customPrecipitate did not form in filtrate like it
  6. concentrationwas concentrated to an oil

Sources & evidence

ORD record
ord-51b76e9366ac4ecfa8c4cabac677da82
Source dataset
uspto-grants-2013_05
Patent number
US08440661B2

Reaction notes

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