Morpholine → HCID 59457492, compound

HRID 1710752Notes

Reaction equation

HRID 1710752 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([C:17]([OH:19])=O)[N:16]=2)=[CH:8][CH:7]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[O:13][CH:14]=[C:15]([C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])[N:16]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59457489HCID 59457489, compound

Product 1

HCID 59457492HCID 59457492, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole-4-carboxylic acid i34 (0.5 g, 1.57 mmol, 1 eq), morpholine (0.15 g, 1.73 mmol, 1.1 eq) and triethylamine (0.44 ml, 3.14 mmol, 2 eq) in dichloromethane (20 ml) is cooled to 0° C. N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.33 g, 1.73 mmol, 1.1 eq) and 1-hydroxybenzotriazole (0.04 g, 0.31 mmol, 0.2 eq) are added to the solution and the mixture is stirred 24 h at room temperature. The mixture is then washed with water and a saturated solution of aqueous ammonium chloride. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum to give 0.54 g of 4-({2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}carbonyl)morpholine i35.

Workup

  1. washThe mixture is then washed with water
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6eb61ffa8b4f433da782cb8cc9e8c79d
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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