Morpholine → HCID 59457474, compound

HRID 1710799Notes

Reaction equation

HRID 1710799 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]([C:18]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)=[O:20])=[C:15]([CH3:17])[N:16]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59457499HCID 59457499, compound

Product 1

HCID 59457474HCID 59457474, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid i106 (1.6 mmol, 1 eq, 0.5 g), triethylamine (3.2 mmol, 2 eq, 0.45 ml) in dichloromethane (20 ml) is added 1-hydroxybenzotriazole (0.32 mmol, 0.2 eq, 43 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (1.76 mmol, 1.1 eq, 0.33 g) and morpholine (1.92 mmol, 1.2 eq, 0.17 g). The mixture is stirred at room temperature overnight. The organic layer is washed with water and with a saturated aqueous solution of ammonium chloride, then dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure. The crude product is purified by flash chromatography over silicagel (eluent: dichloromethane/ethanol 99:1 to 95:5) to afford 380 mg of 4-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}carbonyl)morpholine i107.

Workup

  1. washThe organic layer is washed with water and with a saturated aqueous solution of ammonium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent is removed under reduced pressure
  5. customThe crude product is purified by flash chromatography over silicagel (eluent: dichloromethane/ethanol 99:1 to 95:5)

Sources & evidence

ORD record
ord-9295797ec44a41498b8814e431fe5edd
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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