Benzyl Bromide → HCID 178525717, compound

HRID 1819489Notes

Reaction equation

HRID 1819489 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH2:18]([N:1]([CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178511262HCID 178511262, compound

Product 1

HCID 178525717HCID 178525717, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred slurry of trans-4-aminomethyl-cyclohexanecarboxylic acid (5.00 g, 31.8 mmol) and K2CO3 (4.40 g, 127.2 mmol) in MeOH (100 mL) cooled to 0° C. was added benzyl bromide (7.94 mL, 66.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. Most of the volatiles were removed in vacuo before addition of water (100 mL). The aqueous mixture was extracted with Et2O (2×200 mL) before adjusting to pH 5-6 by addition of 2 N HCl. The aqueous phase was extracted with DCM (3×200 mL) and the combined DCM extracts dried over Na2SO4 before concentrating in vacuo to afford trans-4-[(dibenzylamino)-methyl]-cyclohexanecarboxylic acid (3.22 g, 43%) as an off-white solid, m/z 338 [M+1]+.

Workup

  1. customMost of the volatiles were removed in vacuo before addition of water (100 mL)
  2. extractionThe aqueous mixture was extracted with Et2O (2×200 mL)
  3. additionbefore adjusting to pH 5-6 by addition of 2 N HCl
  4. extractionThe aqueous phase was extracted with DCM (3×200 mL)
  5. dry with materialthe combined DCM extracts dried over Na2SO4
  6. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-245dbf98b2f94aec86533780e6467d2d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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