Morpholine → Ammonia

HRID 385947Notes

Reaction equation

HRID 385947 reaction equation
Br[CH2:2][C:3]1[C:4]([CH3:10])=[N:5][C:6]([Cl:9])=[CH:7][CH:8]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[NH3:5].[Cl:9][C:6]1[N:5]=[C:4]([CH3:10])[C:3]([CH2:2][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 595261743-(Bromomethyl)-6-chloro-2-methylpyridine

Product 2

HCID 222AmmoniaHCID 513419534-[(6-Chloro-2-methylpyridin-3-yl)methyl]morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(Bromomethyl)-6-chloro-2-methylpyridine (500 mg, 2.27 mmol) was taken up in CH2Cl2 (5.0 mL) and morpholine (257 μL, 2.95 mmol) and DIEA (594 μL, 3.40 mmol) were added. After stirring at room temperature overnight, the reaction was diluted with water and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered, and evaporated. Flash chromatography (0-10% MeOH (w/2 M NH3)/CH2Cl2) provided the title compound as a colorless oil.

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d3b4e8cd363f4bcba022ccba1d4517a5
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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