4-(Morpholinomethyl)aniline → HCID 59829924, compound

HRID 1947201Notes

Reaction equation

HRID 1947201 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[C:12]([O:14][CH2:15][CH:16]=[CH2:17])[C:11]([CH2:18][C:19]#[C:20][CH3:21])=[CH:10][C:6]=1[C:7]([OH:9])=O)[CH:2]=[CH2:3].[N:22]1([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH2:1]([O:4][C:5]1[CH:13]=[C:12]([O:14][CH2:15][CH:16]=[CH2:17])[C:11]([CH2:18][C:19]#[C:20][CH3:21])=[CH:10][C:6]=1[C:7]([NH:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[CH:34][CH:33]=1)=[O:9])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 7768514-(Morpholinomethyl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59829865HCID 59829865, compound

Product 1

HCID 59829924HCID 59829924, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,4-bis-allyloxy-5 (but-2-ynyl)-benzoic acid (Example 1-4, IM07-c: 287 mg, 1 mmol) and 4-(morpholin-4-ylmethyl)-phenylamine (IM08-02: 193 mg, 1 mmol) were dissolved in dimethylformamide (4 mL) and mixed with 1-hydroxybenzotriazole monohydrate (176 mg, 1.3 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (249 mg, 1.3 mmol) at 0° C., and the resulting mixture was stirred for 4 hours under ice cold conditions. The reaction mixture was mixed with water (40 mL) and extracted twice with ethyl acetate (50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and then were concentrated. The residue was purified by silica gel column chromatography (hexane-ethylacetate=1:2-1:5) to obtain the title compound (F470-IM09: 0.40 g, yield 82%).

Workup

  1. extractionextracted twice with ethyl acetate (50 mL)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationwere concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethylacetate=1:2-1:5)

Sources & evidence

ORD record
ord-0baf80bcc56c40618d2ce5ed01df2ae0
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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