Morpholine → N-(2-(4-Methoxyphenylthio)ethyl)morpholine-4-carboxamide

HRID 1917070Notes

Reaction equation

HRID 1917070 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:14]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:16])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 12261932Ethanamine, 2-[(4-methoxyphenyl)thio]-

Product 1

HCID 17744820N-(2-(4-Methoxyphenylthio)ethyl)morpholine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 1 (400 mg) in CH2Cl2 (10 mL) was added triphosgene (1.0 eq.) and triethylamine (2.5 eq.) at 0° C. The reaction mixture was stirred for 2 h. at r. t and morpholine (3.0 eq.) was added. The reaction was stirred until it appeared by TLC to be completed (˜4 h), and was washed with 1N HCl and sat NaHCO3 (3×10 mL). The solvents were removed by evaporation under reduced pressure to give product 16 (520 mg). The crude product appeared to be pure by TLC and NMR and used for the next step reaction without further purification.

Workup

  1. stirringThe reaction was stirred until it
  2. custom(˜4 h)
  3. washwas washed with 1N HCl
  4. customThe solvents were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fa3c91ee212346feb833387758b98994
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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