N-Methylbenzylamine → 1-Chloroethyl benzyl(methyl)carbamate

HRID 335535Notes

Reaction equation

HRID 335535 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:11]([O:13][CH:14]([Cl:16])[CH3:15])=[O:12]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:3]([N:2]([CH3:1])[C:11](=[O:12])[O:13][CH:14]([Cl:16])[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 7669N-MethylbenzylamineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 668694551-Chloroethyl benzyl(methyl)carbamateYield 54.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a vigorously stirred suspension of N-methylbenzylamine (0.260 mL, 2 mmol) in EtOAc (3 mL) and 3 mL of saturated NaHCO3 solution was added 1-chloroethyl chloroformate (0.160 mL, 2 mmol). Effervescence was observed. Once gas production had ceased, the reaction mixture was diluted with hexanes (10 mL). The aqueous phase was removed and the organic phase was washed with brine (5 mL), dried and concentrated to give the crude product as an oil (˜0.250 g). The compound was used in the subsequent step without further purification.

Workup

  1. customThe aqueous phase was removed
  2. washthe organic phase was washed with brine (5 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae3db1d73dcd4c48b53334174ca69ee0
Source dataset
uspto-grants-2014_11
Patent number
US08884034B2

Reaction notes

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