1-Chloroethyl chloroformate → 2,2-Dimethylmorpholine hydrochloride

HRID 601562Notes

Reaction equation

HRID 601562 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C:10]([CH3:15])([CH3:14])[CH2:9]1)C1C=CC=CC=1.[Cl:16]C(OC(Cl)C)=O>C(Cl)Cl>[ClH:16].[CH3:14][C:10]1([CH3:15])[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 155791114-Benzyl-2,2-dimethylmorpholine

Product 1

HCID 220368882,2-Dimethylmorpholine hydrochlorideYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-benzyl-2,2-dimethyl-morpholine (5.67 g, 27.6 mmol) in CH2Cl2 (50 mL) and add 1-chloroethyl chloroformate (4.60 mL, 42.2 mmol) while stirring at room temperature. After 4 h, concentrate the solution and treat the residue with MeOH (60 mL). Heat the mixture at 60° C. for 2 h, then concentrate again. Dissolve the residue in water (125 mL) and wash with tert-butyl methyl ether (125 mL). Concentrate the aqueous layer and dry the resulting residue at 80° C. under vacuum to give the title compound (3.91 g, 93%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.52 (2H, br s), 3.75 (2H, m), 2.89-2.96 (4H, m), 1.25 (6H, s).

Workup

  1. concentrationconcentrate the solution
  2. additiontreat the residue with MeOH (60 mL)
  3. temperatureHeat the mixture at 60° C. for 2 h
  4. concentrationconcentrate again
  5. dissolutionDissolve the residue in water (125 mL)
  6. washwash with tert-butyl methyl ether (125 mL)
  7. concentrationConcentrate the aqueous layer
  8. customdry the resulting residue at 80° C. under vacuum

Sources & evidence

ORD record
ord-1b4cf66804c145038ea2c050091a17a2
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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