Triethylamine → HCID 66765157, compound

HRID 594991Notes

Reaction equation

HRID 594991 reaction equation
[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:14]O.C(N(CC)CC)C.S([Cl:27])(C)(=O)=O>C(Cl)Cl>[Cl:27][CH2:14][C:3]1[C:2]([CH3:1])=[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67112254HCID 67112254, compound

Product 1

HCID 66765157HCID 66765157, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2-methyl-3-morpholinophenyl)methanol (0.468 g, 2.26 mmol) was dissolved in dry DCM (14 mL) with triethylamine (0.669 mL, 4.82 mmol) and this stirred solution was cooled at 0° C. in an ice bath. Mesyl chloride (0.415 g, 3.62 mmol) was added dropwise and the reaction was allowed to reach rt overnight. The mixture was diluted in DCM (25 mL), washed with water (20 mL) and the water re-extracted with DCM (20 mL). The combined organics were dried over Na2SO4, filtered and the solvent removed under vacuum to afford 4-(3-(chloromethyl)-2-methylphenyl)morpholine as a crude oil (0.5 g, 98% yield).

Workup

  1. washwashed with water (20 mL)
  2. extractionthe water re-extracted with DCM (20 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-31884f7d0ed8414da92118e7beaf09e4
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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