Benzyl Bromide → HCID 66672581, compound

HRID 1947039Notes

Reaction equation

HRID 1947039 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([O:9][C:8]([CH:5]1[CH2:6][CH2:7][CH:2]([N:1]([CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3][CH2:4]1)=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1715604-Aminocyclohexanecarboxylic acid

Product 1

HCID 66672581HCID 66672581, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

4-Amino-cyclohexanecarboxylic acid (16 g, 0.11 mol) was treated with K2CO3 (46.8 g) in MeCN (225 mL) at 80° C. under Ar. Benzyl bromide (46.6 mL) in MeCN (140 mL) was then added dropwise and stirred at 80° C. for approximately 20 hours and allowed to cool to RT, to yield 4-dibenzylamino-cyclohexanecarboxylic acid benzyl ester (55.04 g) after workup.

Workup

  1. temperatureto cool to RT

Sources & evidence

ORD record
ord-a65d53467fdd48729a68e65e48ee25a1
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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