N-Aminomorpholine → HCID 53950591, compound

HRID 843177Notes

Reaction equation

HRID 843177 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:23])[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:24]=O.[NH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>ClCCl>[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:23])[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:24]=[N:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 20315N-AminomorpholineHCID 22614941HCID 22614941, compound

Product 1

HCID 53950591HCID 53950591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-[3-(methyl-pyridin-3-ylmethyl-amino)-propoxy]-benzofuran-2-carbaldehyde (the compound of Example 115-b) (420 mg) in dichloromethane (50 ml) was added 4-aminomorpholine (380 mg) at room temperature. After stirring overnight, the mixture was washed with water (20 ml), NH4Cl solution (20 ml) and dried over anhydrous sodium sulfate. The mixture was purified by silica gel column chromatography developed by dichloromethane and methanol to give the title compound as a colorless oil (340 mg). ESI-MS: m/z 423 (MH+); 1H-NMR (CDCl3): δ 1.98-2.07 (2H, m), 2.23 (3H, s), 2.30 (3H, s), 2.59 (2H, t, J=6.9 Hz), 3.21-3.26 (4H, m), 3.53 (2H, s), 3.88-3.92 (4H, m), 4.10 (2H, t, J=5.9 Hz), 6.58 (1H, d, J=7.6 Hz), 7.03-7.15 (3H, m), 7.58-7.63 (2H, m), 8.40-8.51 (2H, m).

Workup

  1. washthe mixture was washed with water (20 ml), NH4Cl solution (20 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6139bc34e8c24d288b0a4ab10d89e09e
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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