Dimethyl Sulfoxide → (4-Benzylmorpholin-2-yl)(cyclopropyl)methanone

HRID 30323Notes

Reaction equation

HRID 30323 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([CH:24]([CH:26]2[CH2:28][CH2:27]2)[OH:25])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH:26]1([C:24]([CH:20]2[O:21][CH2:22][CH2:23][N:18]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:19]2)=[O:25])[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59789293(4-Benzylmorpholin-2-yl)(cyclopropyl)methanol

Product 1

HCID 59789271(4-Benzylmorpholin-2-yl)(cyclopropyl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethylsulphoxide (0.69 mL, 9.7 mmol, 2.2 eq) in DCM (4.5 mL) is slowly added to a solution of oxalyl chloride (2.43 mL, 4.85 mmol, 1.1 eq) in DCM (2.5 mL) followed by a solution of 76 (1.09 g, 4.41 mmol) in DCM (0.7 mL) under nitrogen at −60° C. After stirring for 15 minutes, triethylamine (3.14 mL, 22.1 mmol, 5 eq) is added and stirring continues for 15 minutes. After addition of water, the layers are separated.

Workup

  1. stirringstirring
  2. waitcontinues for 15 minutes
  3. customthe layers are separated

Sources & evidence

ORD record
ord-c4081059b5ec48d99cfec68090949e81
Source dataset
uspto-grants-2008_09
Patent number
US07423037B2

Reaction notes

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