Phenethylamine → HCID 18628782, compound

HRID 1060734Notes

Reaction equation

HRID 1060734 reaction equation
Cl[C:2]([CH:4]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:3].[CH2:17]([NH2:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN1CCOCC1>C(OCC)(=O)C>[CH:11]1([CH2:10][CH:4]([C:2]([NH:25][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:3])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 79724-MethylmorpholineHCID 18628711HCID 18628711, compound

Product 1

HCID 18628782HCID 18628782, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of ethyl 2-chlorocarbonyl-3-cyclohexylpropionate (2.65 mmol), phenethylamine (0.376 mL, 3 mmol) and N-methylmorpholine (0.44 mL, 4 mmol) in ethyl acetate (6 mL) was cooled to between −20 and −10° C. and stirred for 15 minutes. The mixture was allowed to warm to room temperature, stirred for approximately 12 hours and then diluted with ethyl acetate (5 mL) and ice (5 mL). The organic layer was separated, washed with cold 0.05 N hydrochloric acid, sodium bicarbonate solution and brine, dried (MgSO4) and concentrated to provide ethyl 2-cyclohexylmethyl-N-phenethylmalonamate (366 mg, 1.106 mmol).

Workup

  1. temperaturewas cooled to between −20 and −10° C.
  2. stirringstirred for approximately 12 hours
  3. customThe organic layer was separated
  4. washwashed with cold 0.05 N hydrochloric acid, sodium bicarbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2eeb6908940848a5b79841cfbc11c8a3
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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