Benzyl Bromide → HCID 178525079, compound

HRID 2111577Notes

Reaction equation

HRID 2111577 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.[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1>CC#N>[CH2:17]([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)[CH2:17][C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 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 K2C03 (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-75a1d10538b34c5285b50708b10bd5f0
Source dataset
uspto-grants-2009_04
Patent number
US07521446B2

Reaction notes

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