Sodium Carbonate → Ethyl (1,2-diphenylethyl)carbamate

HRID 728316

Reaction equation

HRID 728316 reaction equation
[C:1]1([CH:7]([NH2:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(Cl)Cl.O>[C:23]([NH:15][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 264821,2-Diphenylethylamine

Product 1

HCID 234956Ethyl (1,2-diphenylethyl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred two phase solution of 1,2-diphenylethylamine (30.0 g, 0.15 mol) in 300 ml of methylene chloride and 500 ml of water was added sodium carbonate (23.9 g, 0.225 mol) and the solution was cooled to 10° C. under nitrogen. Ethyl chloroformate (21.5 ml, 0.225 mol) was added dropwise over a 1 hour period. The reaction was warmed to ambient temperature and stirred at that temperature for 3 hours. The phases were separated and the aqueous phase was extracted with methylene chloride (75 ml). The combined methylene chloride extracts were washed with 1N HCl (200 ml), dried and evaporated to a white solid, 40.3 g. Recrystallization from cyclohexane gave N-carboethoxy-1,2-diphenylethylamine, mp 74°-75° C.

Workup

  1. temperatureThe reaction was warmed to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene chloride (75 ml)
  4. washThe combined methylene chloride extracts were washed with 1N HCl (200 ml)
  5. customdried
  6. customevaporated to a white solid, 40.3 g
  7. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-fc031b6bbfd04d9ca26179ff63b4af0f
Source dataset
uspto-grants-1991_09
Patent number
US05047541

Linked notes

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